Title: Discover Top Hotels in Winchester, VA | Flexible Booking Choices - Expedia.ca

 

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# Find hotels in Winchester, VA from CA $84

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## Go beyond your typical stay in Winchester

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2025-12-05&d1=2025-12-05&endDate=2025-12-07&d2=2025-12-07&amenities=POOL)

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2025-12-05&d1=2025-12-05&endDate=2025-12-07&d2=2025-12-07&amenities=PETS)

Spa

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2025-12-05&d1=2025-12-05&endDate=2025-12-07&d2=2025-12-07&amenities=SPA_ON_SITE)

Cabin

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2025-12-05&d1=2025-12-05&endDate=2025-12-07&d2=2025-12-07&lodging=CABIN)

Hot tub

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2025-12-05&d1=2025-12-05&endDate=2025-12-07&d2=2025-12-07&amenities=HOT_TUB)

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2025-12-05&d1=2025-12-05&endDate=2025-12-07&d2=2025-12-07&travelerType=family_friendly)

Cottage

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2025-12-05&d1=2025-12-05&endDate=2025-12-07&d2=2025-12-07&lodging=COTTAGE)

Apart­ment

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2025-12-05&d1=2025-12-05&endDate=2025-12-07&d2=2025-12-07&lodging=APARTMENT)

Farm

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2025-12-05&d1=2025-12-05&endDate=2025-12-07&d2=2025-12-07&lodging=AGRITOURISM)

Waterpark

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2025-12-05&d1=2025-12-05&endDate=2025-12-07&d2=2025-12-07&amenities=WATER_PARK)

Chalet

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2025-12-05&d1=2025-12-05&endDate=2025-12-07&d2=2025-12-07&lodging=CHALET)

## Check prices for these dates

Tonight

[Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-11-21&endDate=2025-11-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 22 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-11-22&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Compare 2,029 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/a8e7d0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/d6b37fa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/bff9ad76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The George Washington Hotel, A Wyndham Grand Hotel

Old Town Winchester

9.4/10

Exceptional

(1005)

"Love this hotel and the location. Staff is super friendly. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Casey

CA $178

CA $202 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/d78ffc9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/ffce1877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/41cd029b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Quinta Inn & Suites by Wyndham Winchester

Winchester

9.2/10

Wonderful

(2227)

"A run of the mill motel good for a travel break."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

CARL

CA $131

CA $142 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information)

![Snack bar](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/bf8dce02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/daf3dfdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/c99442ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### TRU By Hilton Winchester

Winchester

9.0/10

Wonderful

(755)

"The hotel was clean and the staff was pleasant."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sherri

CA $112

CA $121 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed, Smoking | Living area](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/38eadba9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed, Smoking](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/8247e5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed, Smoking | Living area](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/fe05e412.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Travelodge by Wyndham Winchester

Winchester

8.6/10

Excellent

(1090)

"Good price, good location "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

George

CA $96

CA $104 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/7ff8d7be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed (Additional Living Area)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/aeec97ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/b6f40366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Winchester Se-Historic Gateway by IHG

Winchester

9.0/10

Wonderful

(1000)

"The room was very clean and the staff were friendly and courteous."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Maria

CA $106

CA $119 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/cd85ec17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/9e37f17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/c7da6581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Winchester

Winchester

9.2/10

Wonderful

(1002)

"Staff are amazing stayed twice in a week and every one was so kind friendly and happy to have us The women who is in the breakfast room was super The rooms where clean and comfortable "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Koren

CA $106

CA $116 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information)

![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/0a2d8398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/3c75b4dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/61e9f06d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/69d352d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Candlewood Suites Winchester by IHG

Winchester

8.8/10

Excellent

(537)

"Very clean room, excellent staff!!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

James

CA $112

CA $121 total

includes taxes & fees

Dec 5 - Dec 6

[](https://www.expedia.ca/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/8897f4a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/5447905f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/e8922549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Microtel Inn & Suites by Wyndham Winchester

Winchester

9.2/10

Wonderful

(1359)

"Excellent accommodations"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Loretta

CA $104

CA $114 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/689131eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/a7fe3c2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/a948cd9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily breakfast for a fee](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/a36008d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Winchester

Winchester

8.8/10

Excellent

(505)

"Great hotel"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

DONNA D

CA $134

CA $152 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Winchester-Hotels-Hilton-Garden-Inn-Winchester.h2169428.Hotel-Information)

![1 bedroom, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/a3d383f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/164a5d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/e6dc1dff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SpringHill Suites by Marriott Winchester

Winchester

9.4/10

Exceptional

(764)

"Clean room, nice area, friendly staff "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

chad

CA $151

CA $164 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/ac575b89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/b2c1f0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/9fc99c66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/1687542a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spark by Hilton Winchester

Winchester

9.0/10

Wonderful

(1001)

"Great location close to restaurants "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

SILVIA

CA $106

CA $120 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information)

![Porch](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/800932de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/16920465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/a888dfb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Winchester-University/Mall Area

Winchester

9.0/10

Wonderful

(1000)

"Staff, clean room, very comfortable bed!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Terri

CA $145

CA $164 total

includes taxes & fees

Nov 27 - Nov 28

[](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/e46c3593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/6a36301f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/f8e3941a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn & Suites Winchester

Winchester

9.4/10

Exceptional

(1052)

"Staff was very friendly, room clean and neat."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Arnold

CA $140

CA $152 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/2000000/1100000/1090600/1090593/38caae92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Japanese garden](https://images.trvl-media.com/lodging/2000000/1100000/1090600/1090593/03cdb617.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room](https://images.trvl-media.com/lodging/2000000/1100000/1090600/1090593/91ceaee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free breakfast](https://images.trvl-media.com/lodging/2000000/1100000/1090600/1090593/c973829f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Hotel & Suites Winchester by IHG

Winchester

9.0/10

Wonderful

(794)

"Great place to stay!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Thomas

CA $134

CA $145 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Hotel-Suites-Winchester.h1090593.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/51a72e04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/b06f3533.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/e0021d58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Country Inn & Suites by Radisson, Winchester, VA

Winchester

8.8/10

Excellent

(1005)

"Have stayed here multiple times -always good"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robert

CA $136

CA $148 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/w4000h2662x0y0-b556d792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/27064e98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/f063e2e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/b20fa3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites by Marriott Winchester

Winchester

9.0/10

Wonderful

(793)

"Quick check in, clean room, friendly staff."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Darcy

CA $130

CA $142 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/8f242b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/5ea79918.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/723a3b2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/1b2ad59b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Courtyard by Marriott Winchester

Winchester

8.8/10

Excellent

(904)

"The staff is very friendly and helpful"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael

CA $150

CA $164 total

includes taxes & fees

Dec 6 - Dec 7

[](https://www.expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information)

![Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/19700/19613/dabc5e45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/19700/19613/226ec321.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/20000/19700/19613/286743b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/19700/19613/174386aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Days Inn by Wyndham Winchester

Winchester

6.6/10

(475)

"Staff was pleasant"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Marie

CA $78

CA $84 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Winchester-Hotels-Days-Inn-By-Wyndham-Winchester.h19613.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/53b7b275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/d2967872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/c9f83fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/decc147c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleep Inn & Suites Winchester near University

Winchester

7.8/10

Good

(1004)

"The rooms were clean and the facility seemed safe and well maintained. The room had seen many patches and repairs and had a distinct smell. The indoor pool, “gym” and breakfast were a plus. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

tyshia

CA $89

CA $97 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information)

![Desk, blackout drapes, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/30000/24100/24072/9bc5a360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/1000000/30000/24100/24072/4ef3053b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Laundry room](https://images.trvl-media.com/lodging/1000000/30000/24100/24072/0e2d3d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24100/24072/ae590780.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Red Roof Inn Winchester, VA

Winchester

7.4/10

Good

(1002)

"Really friendly staff, room was clean and perfect for our family and dog. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sabrina

CA $97

CA $105 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Winchester-Hotels-Red-Roof-Inn-Winchester.h24072.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-05&endDate=2025-12-06&regionId=6056879&adults=2&sort=RECOMMENDED&openPlayBack=true)

## Great weekend hotel deals in Winchester, VA

Showing deals for:**Nov 28 - Nov 30**

![Porch](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)

### Hampton Inn Winchester-University/Mall Area

Winchester

**9.0/10**Wonderful (1,000 reviews)

20% off

CA $145

CA $330 total

includes taxes & fees

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-28&endDate=2025-11-30&selected=19971&adults=2)

![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)

### The George Washington Hotel, A Wyndham Grand Hotel

Winchester

**9.4/10**Exceptional (1,005 reviews)

15% off

CA $286

CA $649 total

includes taxes & fees

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-28&endDate=2025-11-30&selected=1364026&adults=2)

![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)

### Microtel Inn & Suites by Wyndham Winchester

Winchester

**9.2/10**Wonderful (1,359 reviews)

20% off

CA $137

CA $298 total

includes taxes & fees

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-28&endDate=2025-11-30&selected=70921061&adults=2)

![Exterior](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)

### La Quinta Inn & Suites by Wyndham Winchester

Winchester

**9.2/10**Wonderful (2,227 reviews)

20% off

CA $145

CA $316 total

includes taxes & fees

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-28&endDate=2025-11-30&selected=2678524&adults=2)

![Smart TV](https://images.trvl-media.com/lodging/102000000/101420000/101419800/101419784/81dce244.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)

### Cozy Country Getaway in the Heart of Upperville

Upperville

**10/10**Exceptional (16 reviews)

10% off

CA $336

CA $941 total

includes taxes & fees

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-28&endDate=2025-11-30&selected=101419784&adults=2)

![Outdoor dining](https://images.trvl-media.com/lodging/37000000/36630000/36621300/36621280/f0e06430.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)

### Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed

Winchester

**10/10**Exceptional (11 reviews)

10% off

CA $171

CA $667 total

includes taxes & fees

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-28&endDate=2025-11-30&selected=36621280&adults=2)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110440000/110438700/110438645/ecb60c6a.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)

### New Charming 3-bedroom 2 full bath and 1 half bedrooms Single family house

Winchester

**8.4/10**Very good (7 reviews)

10% off

CA $274

CA $975 total

includes taxes & fees

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-28&endDate=2025-11-30&selected=110438645&adults=2)

![Elevator](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)

### Ramada by Wyndham Strasburg/Shenandoah Valley

Strasburg

**8.2/10**Very good (1,003 reviews)

20% off

CA $104

CA $231 total

includes taxes & fees

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-28&endDate=2025-11-30&selected=1246311&adults=2)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/299522c8.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)

### Wayside Inn

Middletown

**9.2/10**Wonderful (414 reviews)

14% off

CA $180

CA $426 total

includes taxes & fees

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-28&endDate=2025-11-30&selected=34467&adults=2)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

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## Check out pet-friendly hotels in Winchester

![Exterior](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/e46c3593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/6a36301f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/f8e3941a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn & Suites Winchester

Winchester

9.4/10

Exceptional

(1052)

CA $140

CA $152 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/8897f4a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/5447905f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/e8922549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Microtel Inn & Suites by Wyndham Winchester

Winchester

9.2/10

Wonderful

(1359)

CA $104

CA $114 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/cd85ec17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/9e37f17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/c7da6581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Winchester

Winchester

9.2/10

Wonderful

(1002)

CA $106

CA $116 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information)

![Snack bar](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/bf8dce02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/daf3dfdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/c99442ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### TRU By Hilton Winchester

Winchester

9.0/10

Wonderful

(755)

CA $112

CA $121 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/d78ffc9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/ffce1877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/41cd029b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Quinta Inn & Suites by Wyndham Winchester

Winchester

9.2/10

Wonderful

(2227)

CA $131

CA $142 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/ac575b89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/b2c1f0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/9fc99c66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/1687542a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spark by Hilton Winchester

Winchester

9.0/10

Wonderful

(1001)

CA $106

CA $120 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information)

![Elevator](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/e47a228e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/9ef74ac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/9fcf0199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ramada by Wyndham Strasburg/Shenandoah Valley

Strasburg

8.2/10

Very good

(1003)

CA $100

CA $112 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/51a72e04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/b06f3533.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/e0021d58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Country Inn & Suites by Radisson, Winchester, VA

Winchester

8.8/10

Excellent

(1005)

CA $136

CA $148 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information)

![In-room safe, desk, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745505/c096d0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![32-inch flat-screen TV with digital channels, TV, Netflix](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745505/7c860f3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745505/802c0401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745505/b1c7d60b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### TownePlace Suites by Marriott Winchester

Winchester

8.8/10

Excellent

(476)

CA $150

CA $164 total

includes taxes & fees

Nov 22 - Nov 23

[](https://www.expedia.ca/Winchester-Hotels-TownePlace-Suites-By-Marriott-Winchester.h2745505.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed, Smoking | Living area](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/38eadba9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed, Smoking](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/8247e5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed, Smoking | Living area](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/fe05e412.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Travelodge by Wyndham Winchester

Winchester

8.6/10

Excellent

(1090)

CA $96

CA $104 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information)

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-05&endDate=2025-12-06&regionId=6056879&adults=2&amenities=PETS&openPlayBack=true)

## Hotels with free breakfast in Winchester you'll enjoy

![Exterior](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/e46c3593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/6a36301f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/f8e3941a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn & Suites Winchester

Winchester

9.4/10

Exceptional

(1052)

CA $140

CA $152 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/8897f4a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/5447905f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/e8922549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Microtel Inn & Suites by Wyndham Winchester

Winchester

9.2/10

Wonderful

(1359)

CA $104

CA $114 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information)

![Elevator](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/e47a228e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/9ef74ac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/9fcf0199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ramada by Wyndham Strasburg/Shenandoah Valley

Strasburg

8.2/10

Very good

(1003)

CA $100

CA $112 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/d78ffc9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/ffce1877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/41cd029b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Quinta Inn & Suites by Wyndham Winchester

Winchester

9.2/10

Wonderful

(2227)

CA $131

CA $142 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information)

![Snack bar](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/bf8dce02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/daf3dfdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/c99442ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### TRU By Hilton Winchester

Winchester

9.0/10

Wonderful

(755)

CA $112

CA $121 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/cd85ec17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/9e37f17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/c7da6581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Winchester

Winchester

9.2/10

Wonderful

(1002)

CA $106

CA $116 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/ac575b89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/b2c1f0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/9fc99c66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/1687542a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spark by Hilton Winchester

Winchester

9.0/10

Wonderful

(1001)

CA $106

CA $120 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/7ff8d7be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed (Additional Living Area)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/aeec97ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/b6f40366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Winchester Se-Historic Gateway by IHG

Winchester

9.0/10

Wonderful

(1000)

CA $106

CA $119 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/w3837h2557x3y3-0ba96f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/afbe118c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/bb49c17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Front Royal

Front Royal

9.0/10

Wonderful

(1002)

CA $139

CA $155 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/10b5cc1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/a71565c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/325feec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/4c979d71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Super 8 by Wyndham Front Royal

Front Royal

7.6/10

Good

(1001)

CA $79

CA $88 total

includes taxes & fees

Nov 22 - Nov 23

[](https://www.expedia.ca/Winchester-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information)

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-05&endDate=2025-12-06&regionId=6056879&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

## Hotels with a pool in Winchester may fit your trip

![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/8897f4a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/5447905f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/e8922549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Microtel Inn & Suites by Wyndham Winchester

Winchester

9.2/10

Wonderful

(1359)

CA $104

CA $114 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information)

![Snack bar](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/bf8dce02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/daf3dfdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/c99442ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### TRU By Hilton Winchester

Winchester

9.0/10

Wonderful

(755)

CA $112

CA $121 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/cd85ec17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/9e37f17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/c7da6581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Winchester

Winchester

9.2/10

Wonderful

(1002)

CA $106

CA $116 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/d78ffc9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/ffce1877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/41cd029b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Quinta Inn & Suites by Wyndham Winchester

Winchester

9.2/10

Wonderful

(2227)

CA $131

CA $142 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/7ff8d7be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed (Additional Living Area)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/aeec97ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/b6f40366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Winchester Se-Historic Gateway by IHG

Winchester

9.0/10

Wonderful

(1000)

CA $106

CA $119 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information)

![1 bedroom, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/a3d383f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/164a5d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/e6dc1dff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SpringHill Suites by Marriott Winchester

Winchester

9.4/10

Exceptional

(764)

CA $151

CA $164 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/w4000h2662x0y0-b556d792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/27064e98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/f063e2e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/b20fa3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites by Marriott Winchester

Winchester

9.0/10

Wonderful

(793)

CA $130

CA $142 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/51a72e04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/b06f3533.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/e0021d58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Country Inn & Suites by Radisson, Winchester, VA

Winchester

8.8/10

Excellent

(1005)

CA $136

CA $148 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information)

![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/ef7d5b18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/71be8e87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/db46282e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/83ee60b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Winchester South-Stephens City by IHG

Stephens City

8.2/10

Very good

(797)

CA $111

CA $121 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/w3837h2557x3y3-0ba96f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/afbe118c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/bb49c17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Front Royal

Front Royal

9.0/10

Wonderful

(1002)

CA $139

CA $155 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-05&endDate=2025-12-06&regionId=6056879&adults=2&amenities=POOL&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

Black Friday Sale

Limited-time deals: save up to 50% on select hotels

[Book now](https://expedia.ca/deals?rfrr=HTG_BF_PROMO_6056879)

## Where to stay in Winchester

Find the best Winchester areas and neighborhoods for the activities you enjoy most.

-   Old Town Winchester
-   Winchester Historic District

![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=6164092)

![Old Town Winchester map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:_wcnFvob%7CMwb%40aMxGad%40bc%40pLeHpd%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=ljIi5EMaahlKlQ6KQ_BYkQvEIhQ=)

### Old Town Winchester

Old Town Winchester is known for its ample dining options, and you can make a stop by Bright Box Theater and Shenandoah Valley Discovery Museum while in the area.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=6164092)

![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=918789051029594112)

![Winchester Historic District map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:ctdnFvsd%7CM%7DI_FCA%5BQeAo%40iAs%40L_%40DB%5E%7BAFDDQDUf%40NDUHBR%7D%40RFLo%40o%40Wc%40USGHeBDuADw%40HaChDM%40ETkCHcAeAG%7B%40Ew%40El%40mFFMFIFGJGHAJ%3FtA%5CRB%5CuC%5BGVwB_CaBaGgEiNmJ%3F%5B%7C%40iFi%40m%40Z%7DBDCHg%40Hq%40F_%40%40SDS%60%40LFi%40F_%40Da%40Fa%40XHR%5BHk%40Hg%40OEHg%40%3FGPgALy%40p%40R%3F_%40L%7B%40%5EJR%3Fd%40LDUBUBONDNDNDNDNDNDNDJBVHPFNBLBn%40PZYb%40L%40%3FRFTaBbAVLDJc%40%5CuBDUN%7B%40MIAAc%40KDUW%40SAK%3Fa%40G_%40KHa%40VcBFQLy%40l%40PRHPFRFCP%7EAd%40BSvA%60%40CRRFVFN%3FNDEZJBND%40%40AFJDbAXGXEXALn%40RpG%7DAf%40ICJk%40zDaFwACb%40Mx%40Kr%40ZJa%40nCd%40NbAX%5CmCTFRDhAXVmB%7C%40VFc%40v%40oFJK%60%40%3FVB%5CDb%40JnCx%40nDbAF_%40RsAT%7DA%7EBp%40hCjAh%40NlBv%40Kn%40_%40bCxA%60%40c%40lDYfBRj%40Kl%40E%5ELDEZ%3F%3FCXNDRFA%40XH%5C%3Fb%40LTFRFRFXHVRf%40NCTCLALCLCRId%40%5B%5EE%5CG%5CXJPDCPCLALCJADA%3FGASIMCGd%40Ib%40Kr%40O%60%40U%7EAHDTDRFEPCRE%5CAJERYIG%60%40Ij%40%5DXM%7C%40ZJG%5ETHABKp%40z%40V%40n%40LD%60%40LZJBM%60%40J%5EJQnAIb%40WlB%7D%40WA%3FECCNy%40Ui%40f%40%5BK%3FAOGMGA%3F%7B%40YEe%40MGq%40Q%3FABIc%40Mi%40O%5BAg%40O_%40KYIYIc%40R%5DKg%40QAJw%40WQw%40q%40Sg%40Oc%40Kc%40Ne%40O%3FDuAa%40%5D%40UIQGFe%40OE%3FBGCKAk%40QCAk%40Oi%40b%40QI%40CSEi%40ODUOES%7CAGFM%60%40QnAMEAJOp%40PFIn%40Id%40Ij%40If%40Ih%40If%40Ij%40Kh%40Gh%40If%40Kl%40Ih%40QG%3FA_ACMTWn%40Uh%40Gl%40Gn%40Id%40AH%3Fn%40%3Fv%40AXJDTx%40Yf%40p%40%5EjA%5EsE%7CY&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=DA_fdKQkDO_rSB3B7g9rdHINaU0=)

### Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112)

### Stay near popular Winchester attractions

Winchester, Virginia, is an excellent destination for outdoor enthusiasts and those seeking scenic beauty. Visitors can explore historic houses and colleges, as well as enjoy leisurely activities by the lake. The area offers a rich cultural experience and family-friendly attractions, perfect for creating lasting memories during your vacation.

[](https://expedia.ca/Museum-Of-The-Shenandoah-Valley-Hotels.0-l6127313-0.Travel-Guide-Filter-Hotels)

![Museum of the Shenandoah Valley](https://mediaim.expedia.com/destination/2/00bcc1929a21a52154c279eaecdf93f9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Museum of the Shenandoah Valley

Experience a captivating blend of art and culture at the Museum of the Shenandoah Valley, showcasing regional history and stunning landscapes in a serene setting.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6127313)

[](https://expedia.ca/Handley-Regional-Library-Hotels.0-l6164024-0.Travel-Guide-Filter-Hotels)

![Handley Regional Library](https://mediaim.expedia.com/destination/2/73997bc29c1a471c7123089852c4944b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Handley Regional Library

Explore Handley Regional Library, a vibrant hub of family and culture, where you can immerse yourself in a welcoming atmosphere and discover a wealth of resources and activities.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6164024)

[](https://expedia.ca/Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels)

#### Winchester Medical Center

Though Winchester Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Winchester while you are here.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6164057)

[](https://expedia.ca/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels)

#### Shenandoah University

Experience the rich culture and historic charm of Shenandoah University, where vibrant campus life and picturesque surroundings create a unique and engaging atmosphere for visitors.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6127311)

[](https://expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels)

#### Apple Blossom Mall

Apple Blossom Mall offers a vibrant shopping experience with family-friendly stores, entertainment options, and a mix of local and brand-name shops perfect for all ages.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6164018)

[](https://expedia.ca/Shenandoah-Valley-Discovery-Museum-Hotels.0-l553248621587527659-0.Travel-Guide-Filter-Hotels)

#### Shenandoah Valley Discovery Museum

Explore the interactive exhibits of Shenandoah Valley Discovery Museum, where families can enjoy engaging activities that celebrate the region's culture and foster a love for learning.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621587527659)

## More cheap stays in Winchester

![Hampton Inn Martinsburg](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/835cd022_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Hampton Inn Martinsburg

975 Foxcroft Ave Martinsburg WV

CA $117

CA $132 total

Dec 15 - Dec 16

includes taxes & fees

8.4/10 Very Good! (964 reviews)

[](https://expedia.ca/Martinsburg-Hotels-Hampton-Inn-Martinsburg.h63064.Hotel-Information)

![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA

CA $96

CA $104 total

Dec 14 - Dec 15

includes taxes & fees

8.4/10 Very Good! (1,085 reviews)

[](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information)

![Ramada by Wyndham Strasburg/Shenandoah Valley](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Ramada by Wyndham Strasburg/Shenandoah Valley

21 Signal Knob Dr Strasburg VA

CA $100

CA $112 total

Dec 21 - Dec 22

includes taxes & fees

8.2/10 Very Good! (1,003 reviews)

[](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information)

![Baymont by Wyndham Warrenton](https://images.trvl-media.com/lodging/1000000/20000/10100/10086/ad87d83f_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Baymont by Wyndham Warrenton

7379 Comfort Inn Drive Warrenton VA

CA $93

CA $100 total

Nov 29 - Nov 30

includes taxes & fees

6.4/10 (1,003 reviews)

[](https://expedia.ca/Warrenton-Hotels-Baymont-By-Wyndham-Warrenton.h10086.Hotel-Information)

![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Comfort Inn & Suites Winchester

195 Kernstown Commons Blvd Winchester VA

CA $140

CA $152 total

Nov 23 - Nov 24

includes taxes & fees

9.4/10 Exceptional! (1,050 reviews)

[](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information)

![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza Winchester VA

CA $104

CA $114 total

Dec 14 - Dec 15

includes taxes & fees

9/10 Wonderful! (1,353 reviews)

[](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information)

## Hotels in Winchester with star-rating

![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg)

5 Star Hotels

2 properties

[](https://expedia.ca/5Star-Winchester-Hotels.s50-0-d6056879.Travel-Guide-Filter-Hotels)

![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg)

4 Star Hotels

18 properties

[](https://expedia.ca/4Star-Winchester-Hotels.s40-0-d6056879.Travel-Guide-Filter-Hotels)

![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg)

3 Star Hotels

249 properties

[](https://expedia.ca/3Star-Winchester-Hotels.s30-0-d6056879.Travel-Guide-Filter-Hotels)

![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg)

2 Star Hotels

248 properties

[](https://expedia.ca/2Star-Winchester-Hotels.s20-0-d6056879.Travel-Guide-Filter-Hotels)

## Find out more about Winchester

### Top reasons to visit Winchester

-   **Outdoor Adventures:** Winchester offers stunning scenery and recreational areas, perfect for nature lovers and adventure seekers.
-   **Rich Historical Heritage:** Explore historic houses and sites to immerse yourself in Winchester's fascinating past.
-   **Charming Downtown:** Stroll through the vibrant downtown filled with unique shops and family-friendly attractions.
-   **Variety of Accommodations:** From pet-friendly hotels to business-themed lodgings, there's something for every traveller.
-   **Scenic Lakes:** Enjoy the beautiful local lakes, ideal for relaxing and outdoor activities.

### Find great hotels in Winchester

Winchester, Virginia offers a diverse selection of accommodations, catering to various preferences and needs. From pet-friendly options to business-themed hotels and LGBTQIA welcoming stays, you'll find the perfect fit for your vacation. Explore comfortable suites and star-rated hotels that provide a memorable experience in this charming town, ensuring a delightful retreat for all travellers.

-   **[Travelodge by Wyndham Winchester:](https://www.expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information)** Nestled in the heart of Winchester, Travelodge by Wyndham offers a welcoming atmosphere for those travelling with pets. This motel-style lodging prioritizes comfort and convenience, making it an ideal choice for pet owners. With amenities such as pet-friendly rooms, you can enjoy your stay without leaving your furry friends behind. The property’s emphasis on a casual, laid-back experience makes it perfect for travellers seeking a relaxed getaway.
-   **[La Quinta Inn & Suites by Wyndham Winchester:](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information)** La Quinta Inn & Suites combines business and leisure in a vibrant setting. This hotel is particularly welcoming to the LGBTQIA community and provides a range of business amenities, including multiple meeting rooms and an accessible business centre. Ideal for both professionals and leisure travellers, it allows pets and offers comfortable rooms that cater to everyone. Enjoy a stay that prioritizes inclusivity and convenience, perfect for those looking to blend work with relaxation.
-   **Red Roof Inn Winchester, VA:** Red Roof Inn is a family-friendly hotel that welcomes both children and pets, making it a great choice for families travelling together. The property prides itself on being LGBTQIA welcoming and ensuring a comfortable stay for all guests. With amenities designed for children, including free cribs, families can rest easy knowing their needs are catered to. With pet-friendly policies and a relaxed atmosphere, this hotel ensures everyone feels at home during their stay.

### Things to do in and around Winchester

Winchester, Virginia, is perfect for outdoor enthusiasts and adventure seekers, boasting stunning scenery and recreational areas. Visitors can explore top attractions, enjoy shopping centres, and experience the vibrant nightlife. Whether you're skiing or engaging in educational activities, Winchester offers a variety of experiences that cater to all interests, making it an ideal vacation destination for Canadian tourists.

**Shopping**

In Winchester, you can shop at [Apple Blossom Mall](https://www.expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) for a variety of stores and entertainment. [Nalls Farm Market](https://www.expedia.ca/Nalls-Farm-Market-Hotels.0-l553248621532661846-0.Travel-Guide-Filter-Hotels) offers local goods, while Apple Valley Square Shopping Center has a great selection of shops. If you're up for a drive, explore nearby towns for unique boutiques and gifts.

**Recreation**

Enjoy a round of golf at [Rock Harbor Golf Course](https://www.expedia.ca/Rock-Harbor-Golf-Course-Hotels.0-l553248621561864838-0.Travel-Guide-Filter-Hotels), surrounded by beautiful landscapes and a vibrant outdoor atmosphere. For relaxation, visit [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Hotels.0-l6164028-0.Travel-Guide-Filter-Hotels), where you can unwind amidst nature. Alternatively, head to [Appleland Sports Center](https://www.expedia.ca/Appleland-Sports-Center-Hotels.0-l553248621587477489-0.Travel-Guide-Filter-Hotels) for a variety of wellness activities, just 9.7km from Winchester.

**Adventure**

At [Summit Point Motorsports Park](https://www.expedia.ca/Summit-Point-Motorsports-Park-Hotels.0-l6164103-0.Travel-Guide-Filter-Hotels), experience the thrill of motor racing in a vibrant atmosphere, located 17.7km from Winchester. [Watermelon Park Campground](https://www.expedia.ca/Watermelon-Park-Campground-Hotels.0-l553248621532661928-0.Travel-Guide-Filter-Hotels) offers a family-friendly outdoor adventure, situated 20.9km away. For a scenic hike, [Tuckers Lane Trailhead](https://www.expedia.ca/Tuckers-Lane-Trailhead-Hotels.0-l553248633992585760-0.Travel-Guide-Filter-Hotels) awaits, 32.2km from the city, perfect for nature lovers.

**Nightlife**

Winchester’s nightlife offers a variety of experiences. Enjoy a show at [Bright Box Theater](https://www.expedia.ca/Bright-Box-Theater-Hotels.0-l553248621561864843-0.Travel-Guide-Filter-Hotels) or the [Winchester Little Theater](https://www.expedia.ca/Winchester-Little-Theater-Hotels.0-l6164047-0.Travel-Guide-Filter-Hotels), both exuding culture and romance. For a unique twist, venture 33.8km to the [Morgan County Observatory](https://www.expedia.ca/Morgan-County-Observatory-Hotels.0-l553248621558141373-0.Travel-Guide-Filter-Hotels) for a night of stargazing and entertainment vibes.

*\*Distances are measured in a straight line; actual driving distances may vary depending on the route.*

### Booking tips and Expedia advantages for Winchester

Winchester, Virginia, offers numerous ways to save during your visit. Enjoy free attractions like Shenandoah University and Mackintosh Fruit Farm, and consider walking or biking to explore the city. The best time to visit is from January to March when accommodation prices drop, with Tuesdays being the least expensive days to stay. Use Expedia to find budget-friendly hotels and combine your flight and hotel for added savings. Look for eco-certified options to support sustainability while securing great deals and unlocking travel rewards for future trips.

-   **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Winchester are January to March, where the prices are slightly lower. This is in comparison to May to June and October, where prices are slightly higher.
-   **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Winchester is Tuesday. The most expensive day to stay in Winchester is Saturday.
-   **Find cheap hotels on Expedia:** Expedia’s search tool empowers you to set your budget, choose your desired location, and more. You can arrange your search results from lowest to highest price, making it easy to find the most affordable accommodations first. Additionally, you have the option to refine your choices by hotel category; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that you can book.
-   **Consider bundling your trip:** You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package.

### Find the best attractions in Winchester

Winchester, Virginia, offers a delightful blend of outdoor adventures and rich cultural experiences. Visitors can explore historic houses and sites, enjoy the scenic beauty of local lakes, and immerse themselves in the region's history. Whether you're seeking exciting family activities or a deeper understanding of Winchester's heritage, there's something for everyone in this charming city.

-   **[Shenandoah University:](https://www.expedia.ca/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels)** Immerse yourself in the vibrant culture of Shenandoah University, a historic institution in Winchester. Explore its beautiful campus, featuring historic architecture and a lively student atmosphere that reflects the region's rich educational heritage.
-   **[Museum of the Shenandoah Valley:](https://www.expedia.ca/Museum-Of-The-Shenandoah-Valley-Hotels.0-l6127313-0.Travel-Guide-Filter-Hotels)** Discover the Museum of the Shenandoah Valley, an art museum that showcases the region's history and artistic talent. With diverse exhibits, gardens, and stunning collections, it's a perfect spot for art lovers and history buffs alike.
-   **[Shenandoah Valley Discovery Museum:](https://www.expedia.ca/Shenandoah-Valley-Discovery-Museum-Hotels.0-l553248621587527659-0.Travel-Guide-Filter-Hotels)** A family-friendly destination, the Shenandoah Valley Discovery Museum offers interactive exhibits and engaging activities for children. It's an educational haven where families can learn about the valley's ecology and history in a fun, hands-on way.

### Best time to go to Winchester

The best time to visit Winchester is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

| **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** |
| --- | --- | --- | --- | --- | --- |
| January | 31.3°F (-0.4°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low |
| February | 34.7°F (1.5°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low |
| March | 42.3°F (5.7°C) | Light Rain | Mostly Sunny | Average | Slightly Low |
| April | 52.9°F (11.6°C) | Light Rain | Mostly Sunny | Average | Average |
| May | 62.4°F (16.9°C) | Light Rain | Mostly Sunny | Average | Slightly High |
| June | 70.9°F (21.6°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High |
| July | 75.9°F (24.4°C) | Light Rain | Mostly Sunny | Slightly High | Average |
| August | 73.8°F (23.2°C) | Light Rain | Mostly Sunny | Average | Average |
| September | 66.9°F (19.4°C) | Light Rain | Mostly Sunny | Average | Average |
| October | 55.8°F (13.2°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High |
| November | 43.5°F (6.4°C) | Light Rain | Mostly Sunny | Average | Average |
| December | 36.7°F (2.6°C) | Light Rain | Mostly Sunny | Slightly Low | Average |

### The nearest major airports for your trip to Winchester

When visiting Winchester, Virginia, you have a few airport options to consider. Washington Dulles International Airport ([IAD](https://www.expedia.ca/Washington-Dulles-Intl-Airport-Hotels.0-aIAD-0.Travel-Guide-Filter-Hotels)) is 67.6km away and offers several nearby accommodations, such as the 4-star [Hyatt Regency Dulles](https://www.expedia.ca/Herndon-Hotels-Hyatt-Regency-Dulles.h150.Hotel-Information), just one mile from the airport, and the [Hilton Washington Dulles Airport](https://www.expedia.ca/Herndon-Hotels-Hilton-Washington-Dulles-Airport.h27218.Hotel-Information), two miles away. Hagerstown Regional Airport ([HGR](https://www.expedia.ca/Hagerstown-Regional-Airport-Hotels.0-aHGR-0.Travel-Guide-Filter-Hotels)) is 69.2km from Winchester, with options like the Mercersburg Inn, 19.3km away, and Springhill Suites by Marriott, six miles away. Lastly, Eastern West Virginia Regional Airport (MRB) is only 29.0km from Winchester, featuring hotels like the [Hillbrook Inn](https://www.expedia.ca/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information), 17.7km away, and Home2 Suites by Hilton, three miles away.

## Recent reviews of Winchester hotels

![Country Inn & Suites by Radisson, Winchester, VA](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg)

### Country Inn & Suites by Radisson, Winchester, VA

5/5 Excellent

"As long as I don’t experience anything negative then my stay was great "

A verified traveller stayed at Country Inn & Suites by Radisson, Winchester, VA

Posted 14 hours ago

[](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information)

![Hampton Inn Winchester N/Conference Center, VA](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/cba33bb0_y.jpg)

### Hampton Inn Winchester N/Conference Center, VA

5/5 Excellent

"Breakfast was fresh. Front desk staff very friendly and helpful. Rooms are clean, bathroom was great. "

A verified traveller stayed at Hampton Inn Winchester N/Conference Center, VA

Posted 3 days ago

[](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information)

![Holiday Inn Winchester Se-Historic Gateway by IHG](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg)

### Holiday Inn Winchester Se-Historic Gateway by IHG

5/5 Excellent

"Clean, quiet room. Very friendly service. The bar and restaurant, when open, is very nice and convenient. "

A verified traveller stayed at Holiday Inn Winchester Se-Historic Gateway by IHG

Posted 4 days ago

[](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information)

![Courtyard by Marriott Winchester](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/8f242b36_y.jpg)

### Courtyard by Marriott Winchester

5/5 Excellent

"The staff is very friendly and helpful"

A verified traveller stayed at Courtyard by Marriott Winchester

Posted 4 days ago

[](https://expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information)

![Quality Inn Winchester](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943_y.jpg)

### Quality Inn Winchester

5/5 Excellent

"Staff are amazing stayed twice in a week and every one was so kind friendly and happy to have us The women who is in the breakfast room was super The rooms where clean and comfortable "

A verified traveller stayed at Quality Inn Winchester

Posted 4 days ago

[](https://expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information)

![SpringHill Suites by Marriott Winchester](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05_y.jpg)

### SpringHill Suites by Marriott Winchester

5/5 Excellent

"Excellent, highly recommend!!!"

A verified traveller stayed at SpringHill Suites by Marriott Winchester

Posted 5 days ago

[](https://expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information)

![Candlewood Suites Winchester by IHG](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/0a2d8398_y.jpg)

### Candlewood Suites Winchester by IHG

5/5 Excellent

"Clean rooms, great shower water pressure, friendly staff "

A verified traveller stayed at Candlewood Suites Winchester by IHG

Posted 5 days ago

[](https://expedia.ca/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.Hotel-Information)

![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg)

### The George Washington Hotel, A Wyndham Grand Hotel

5/5 Excellent

"The room was perfect. Clean, spacious and the staff was very friendly. Also loved happy hour at the bar, great drinks and appetizers. "

A verified traveller stayed at The George Washington Hotel, A Wyndham Grand Hotel

Posted 5 days ago

[](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg)

### La Quinta Inn & Suites by Wyndham Winchester

5/5 Excellent

"Thank you "

A verified traveller stayed at La Quinta Inn & Suites by Wyndham Winchester

Posted 6 days ago

[](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information)

## Frequently asked questions

### What are the best hotels in Winchester with outdoor pools?

> [Quality Inn Winchester](https://www.expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) is a fantastic choice for travellers seeking comfort and convenience, featuring an inviting outdoor pool that adds to its family-friendly appeal. Guests consistently rave about the clean, comfortable rooms and the excellent, friendly staff, earning the hotel an excellent review rating of 9.2. Start your day off right with a free breakfast that many guests describe as good, making it a great value for families on the go.
> 
>   
> 
> [Hampton Inn Winchester N/Conference Center, VA](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) also shines in the outdoor pool category, providing a refreshing space for relaxation after a day of exploration. With a matching review score of 9.2, this hotel impresses visitors with its friendly and helpful staff, as well as its comfortable rooms. The complimentary breakfast buffet is another highlight that families appreciate, adding to the convenience of their stay.
> 
>   
> 
> For those who prefer a hotel near shopping and university areas, [Hampton Inn Winchester-University/Mall Area](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) is a solid option featuring an outdoor pool. With a traveller rating of 9.0, guests praise the staff for being friendly and amazing, while praising the clean rooms and great breakfast offerings. The location makes it superb for families looking to explore local attractions.
> 
>   
> 
> [Courtyard by Marriott Winchester](https://www.expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information), though primarily offering an indoor pool, also caters to families looking for a comfortable stay with a review score of 8.8. Its amenities, including spacious suites and convenient self-parking, make it a practical choice for travellers.
> 
>   
> 
> Lastly, [TownePlace Suites by Marriott Winchester](https://www.expedia.ca/Winchester-Hotels-TownePlace-Suites-By-Marriott-Winchester.h2745505.Hotel-Information) features an outdoor pool and is known for its attentive staff and spotless rooms, also scoring an 8.8. Families will appreciate the free continental breakfast and the good coffee available, ensuring a pleasant start to their day.

### How much does a hotel with outdoor pool in Winchester cost?

> Enjoy staying in a hotel in Winchester with an outdoor pool. You can find a great deal from CA $84 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.

### Is it cheaper to book flights and a hotel in Winchester as a package?

> Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect [travel package](https://www.expedia.ca/Winchester.d6056879.Destination-Travel-Guides).

### How can I save on a hotel in Winchester with Expedia?

> Before booking your Winchester hotel, remember to join Expedia's free travel rewards program—[One Key™](https://www.expedia.ca/welcome-one-key). Just sign up and sign in to access our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.

### Can I cancel my hotel reservation on Expedia?

> Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel with an outdoor pool in Winchester for you.

### What are the best hotels in Winchester with free breakfast and a fitness center?

> For hotels in Winchester offering both free breakfast and a fitness centre, excellent choices include [Comfort Inn & Suites Winchester](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information), [SpringHill Suites by Marriott Winchester](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information), and [La Quinta Inn & Suites by Wyndham Winchester](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information).
> 
>   
> 
> Comfort Inn & Suites Winchester has a high review rating of 9.4. Guests frequently praise the comfortable and clean rooms, as well as the excellent and friendly staff. The free breakfast is noted as good, and the hotel also provides a 24-hour accessible fitness centre.
> 
>   
> 
> SpringHill Suites by Marriott Winchester, also with a 9.4 rating, is another fantastic option. Reviewers often highlight the comfortable rooms, friendly staff, and excellent free breakfast. This hotel also features a 24-hour accessible fitness centre and a clean, warm pool.
> 
>   
> 
> The 3-star La Quinta Inn & Suites by Wyndham Winchester, with a 9.2 rating, offers nice and clean rooms. Guests appreciate the friendly and helpful staff, along with a good free buffet breakfast.

### Which Winchester hotels with free breakfast have the best customer service?

> For Winchester hotels with complimentary breakfast and excellent customer service, travellers frequently recommend [Comfort Inn & Suites Winchester](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information), [SpringHill Suites by Marriott Winchester](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information), and [La Quinta Inn & Suites by Wyndham Winchester](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information).
> 
>   
> 
> The Comfort Inn & Suites Winchester, with a fantastic 9.4 rating, consistently receives praise for its great customer service and friendly, excellent staff. Guests particularly appreciate the free self-serve breakfast and complimentary WiFi, ensuring a comfortable and convenient stay.
> 
>   
> 
> Another superb choice is the SpringHill Suites by Marriott Winchester, also boasting a 9.4 rating. Reviewers often highlight the friendly and good staff. This hotel offers a free continental breakfast, free WiFi, and even free parking for RVs, buses, and trucks, adding to its great value.
> 
>   
> 
> The 3-star La Quinta Inn & Suites by Wyndham Winchester, rated 9.2, is known for its friendly and helpful staff and great customer service.

### How can I save on a hotel in Winchester with Expedia?

> With Expedia, you'll unlock our lowest prices by becoming a [One Key™](https://www.expedia.ca/welcome-one-key) member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Winchester hotels with free breakfast. Typically, booking in advance will help you save on your hotel stay. If you're feeling spontaneous, be sure to check for last-minute deals.

### Can I cancel my hotel reservation on Expedia?

> Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel with free breakfast in Winchester for you.

### What are the best family hotels in Winchester that have a spa?

> [The George Washington Hotel, A Wyndham Grand Hotel](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) is an excellent choice for families seeking a blend of comfort and relaxation in Winchester. This 3.5-star hotel boasts an impressive onsite spa where guests can indulge in rejuvenating massages and full-service treatments, ideal for parents looking to unwind while the kids are entertained.
> 
>   
> 
> Guests have praised the hotel for its comfortable and clean rooms, with an excellent traveller rating of 9.4. Families appreciate the modern amenities, including free WiFi and toiletries, which ensure a straightforward stay. The friendly and helpful staff are always on hand to assist, adding to the welcoming atmosphere that makes this hotel a favourite among family travellers.
> 
>   
> 
> Moreover, the hotel's convenient location and easy, free parking make it a stress-free option for those exploring the charming attractions of Winchester.

### Are there any great family hotels in Winchester with a gym?

> The [Comfort Inn & Suites Winchester](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) is a fantastic choice for families looking for a hotel with a gym. Rated an impressive 9.4 by travellers, this hotel offers comfortable and clean rooms, along with excellent and friendly staff. Guests particularly appreciate the free breakfast, which is a great convenience for busy mornings, and the location is known for being both close and convenient.
> 
>   
> 
> Another excellent option is [The George Washington Hotel, A Wyndham Grand Hotel](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information), also boasting a review score of 9.4. This hotel features modern amenities and a friendly, helpful staff, making it a welcoming place for families. With its accessible 24-hour fitness centre, families can easily keep up with their workout routines while enjoying their stay.
> 
>   
> 
> For those who prefer a more contemporary vibe, the [SpringHill Suites by Marriott Winchester](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) is another stellar choice, featuring a fitness centre that is also accessible. Rated 9.4 by guests, it's praised for its comfortable rooms and excellent free breakfast. Families will enjoy the pool as well, ensuring a fun and relaxing experience after a day of exploring.
> 
>   
> 
> [La Quinta Inn & Suites by Wyndham Winchester](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information), with a rating of 9.2, is also a family-friendly option that includes fitness facilities. Guests love the convenient location and the clean, nice rooms, making it a good base for family adventures.
> 
>   
> 
> Lastly, the [Microtel Inn & Suites by Wyndham Winchester](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information), similarly rated at 9.2, offers a cozy atmosphere with accessible fitness facilities and a friendly staff.

### How can I save on a family-friendly hotel in Winchester with Expedia?

> With Expedia, you'll unlock our lowest prices by becoming a [One Key™](https://www.expedia.ca/welcome-one-key) member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on family-friendly Winchester hotels. Typically, booking in advance will help you save on your hotel stay. If you're feeling spontaneous, be sure to check for last-minute deals.

### Can I cancel my family hotel reservation on Expedia?

> Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right family-friendly hotel in Winchester for you.

### Is it cheaper to book flights and a hotel in Winchester as a package?

> Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect [travel package](https://www.expedia.ca/Winchester.d6056879.Destination-Travel-Guides).

### Can I cancel my budget hotel reservation on Expedia?

> Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right budget hotel in Winchester for you.

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-   [Hotels near Winchester-Frederick County Convention & Visitors Bureau](https://www.expedia.ca/Winchester-Frederick-County-Convention-Visitors-Bureau-Hotels.0-l553248621561864842-0.Travel-Guide-Filter-Hotels)
-   [Hotels with Bar in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Hotels-With-Bar.0-n918789051029594112-0-tHotelswithBar.Travel-Guide-Filter-Hotels)
-   [Pet-Friendly Hotels in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Pet-Friendly-Hotel.0-n918789051029594112-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Spa Hotels in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Spa-Hotel.0-n918789051029594112-0-tSpaHotel.Travel-Guide-Filter-Hotels)
-   [Hotels near Winchester Medical Center](https://www.expedia.ca/Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels)

-   [Flights to Boyce](https://www.expedia.ca/Cheap-Flights-To-Boyce.d184084.Travel-Guide-Flights)
-   [Flights to Millwood](https://www.expedia.ca/Cheap-Flights-To-Millwood.d3000460156.Travel-Guide-Flights)
-   [Flights from Winchester Regional](https://www.expedia.ca/lp/airports/wgo/flights-from-winchester-regional-airport)
-   [Flights from Gore](https://www.expedia.ca/lp/flights/3000460015/flights-from-gore)
-   [Flights from Clear Brook](https://www.expedia.ca/lp/flights/553248635975870250/flights-from-clear-brook)
-   [Flights from Blacksburg (BCB) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bcb/wgo/blacksburg-to-winchester)
-   [Flights from Hartford (BDL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bdl/wgo/hartford-to-winchester)
-   [Flights from Baltimore (BWI) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bwi/wgo/baltimore-to-winchester)
-   [Flights from Denver (DEN) to Winchester (WGO)](https://www.expedia.ca/lp/flights/den/wgo/denver-to-winchester)
-   [Flights from Dallas (DFW) to Winchester (WGO)](https://www.expedia.ca/lp/flights/dfw/wgo/dallas-to-winchester)
-   [Flights from El Paso (ELP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/elp/wgo/el-paso-to-winchester)
-   [Flights from Fort Lauderdale (FLL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/fll/wgo/fort-lauderdale-to-winchester)
-   [Flights from Greenville (GSP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/gsp/wgo/greenville-to-winchester)
-   [Flights from Jacksonville (JAX) to Winchester (WGO)](https://www.expedia.ca/lp/flights/jax/wgo/jacksonville-to-winchester)
-   [Flights from Melbourne (MEL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/mel/wgo/melbourne-to-winchester)
-   [Flights from Sarasota (SRQ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/srq/wgo/sarasota-to-winchester)
-   [Flights from Syracuse (SYR) to Winchester (WGO)](https://www.expedia.ca/lp/flights/syr/wgo/syracuse-to-winchester)
-   [Flights from Calgary (YYC) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyc/wgo/calgary-to-winchester)
-   [Flights from Toronto (YYZ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyz/wgo/toronto-to-winchester)

-   [Appleland Sports Center](https://www.expedia.ca/Appleland-Sports-Center-Stephens-City.d553248621587477489.Vacation-Attraction)
-   [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction)
-   [Visit Millwood](https://www.expedia.ca/Millwood.dx3000460156)

-   [Book Hotels in Winchester on Expedia.com](https://www.expedia.com/Winchester-Hotels.d6056879.Travel-Guide-Hotels)

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![QR code to download the app](data:image/png;base64,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)