Title: 10 Best Hotels in Old Town Winchester, Winchester for 2025 | Expedia.ca

  

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# Hotels in Old Town Winchester, Winchester

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## Go beyond your typical stay in Old Town Winchester

Cabin

[](https://www.expedia.ca/Hotel-Search?destination=Old+Town+Winchester%2C+Winchester%2C+Virginia%2C+United+States+of+America&regionId=6164092&latLong=39.18421%2C-78.16561&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=CABIN)

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Old+Town+Winchester%2C+Winchester%2C+Virginia%2C+United+States+of+America&regionId=6164092&latLong=39.18421%2C-78.16561&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&travelerType=family_friendly)

Apart­ment

[](https://www.expedia.ca/Hotel-Search?destination=Old+Town+Winchester%2C+Winchester%2C+Virginia%2C+United+States+of+America&regionId=6164092&latLong=39.18421%2C-78.16561&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=APARTMENT)

Cottage

[](https://www.expedia.ca/Hotel-Search?destination=Old+Town+Winchester%2C+Winchester%2C+Virginia%2C+United+States+of+America&regionId=6164092&latLong=39.18421%2C-78.16561&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=COTTAGE)

Hot tub

[](https://www.expedia.ca/Hotel-Search?destination=Old+Town+Winchester%2C+Winchester%2C+Virginia%2C+United+States+of+America&regionId=6164092&latLong=39.18421%2C-78.16561&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=HOT_TUB)

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Old+Town+Winchester%2C+Winchester%2C+Virginia%2C+United+States+of+America&regionId=6164092&latLong=39.18421%2C-78.16561&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=POOL)

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Old+Town+Winchester%2C+Winchester%2C+Virginia%2C+United+States+of+America&regionId=6164092&latLong=39.18421%2C-78.16561&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=PETS)

## Check prices for these dates

Tonight

[Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Recommended

Price (low to high)

Distance

Star rating

## Old Town Winchester hotels and places to stay

![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)

![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)

![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/a8e7d0d0.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)

"Very nice hotel "

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

Paul

CA $177

CA $200 total

includes taxes & fees

Nov 6 - Nov 7

[](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)

![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/41cd029b.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)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/b1a55fc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Quinta Inn & Suites by Wyndham Winchester

2.9 km from Old Town Winchester

9.2/10

Wonderful

(2189)

"Great hotel"

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

David

CA $143

CA $156 total

includes taxes & fees

Nov 2 - Nov 3

[](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)

![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)

![Lobby](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/76fedaf8.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

4.4 km from Old Town Winchester

9.0/10

Wonderful

(737)

"Friendly staff, convenient location "

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

Dahai

CA $123

CA $134 total

includes taxes & fees

Nov 26 - Nov 27

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

![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/1e2a7464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/d7931645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room, 2 Double Beds, Smoking](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/65ba6c12.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/1000000/10000/9600/9600/28616e5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Travelodge by Wyndham Winchester

2.9 km from Old Town Winchester

8.6/10

Excellent

(1116)

"It's been a great stay so far"

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

Sabrina

CA $96

CA $105 total

includes taxes & fees

Nov 2 - Nov 3

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

![Lobby](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/037b096c.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)

### Hilton Garden Inn Winchester

2.1 km from Old Town Winchester

8.8/10

Excellent

(500)

"Great hotel"

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

DONNA D

CA $133

CA $151 total

includes taxes & fees

Nov 9 - Nov 10

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

![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)

![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)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/ee4df7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

3.2 km from Old Town Winchester

9.0/10

Wonderful

(1000)

"Great stay value"

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

Timothy

CA $103

CA $116 total

includes taxes & fees

Nov 30 - Dec 1

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

![Breakfast meal](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/a5945e18.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)

![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)

### Candlewood Suites Winchester by IHG

3.1 km from Old Town Winchester

8.8/10

Excellent

(528)

"Lots of parking. "

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

Douglas

CA $141

CA $153 total

includes taxes & fees

Nov 2 - Nov 3

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

![Breakfast area](https://images.trvl-media.com/lodging/1000000/860000/856400/856310/8753a03f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed with Sofa bed, Smoking](https://images.trvl-media.com/lodging/1000000/860000/856400/856310/3c65e97c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Laundry room](https://images.trvl-media.com/lodging/1000000/860000/856400/856310/92453303.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/860000/856400/856310/78b01efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Econo Lodge Inn & Suites

19.3 km from Old Town Winchester

5.8/10

(292)

"I loved staying here!"

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

Whitney

CA $87

CA $96 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Middletown-Hotels-Econo-Lodge-Inn-Suites.h856310.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)

![Lobby](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/be9a8325.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)

### Ramada by Wyndham Strasburg/Shenandoah Valley

25.8 km from Old Town Winchester

8.2/10

Very good

(1001)

"Our stay was fine, convenient location to our planned activities. "

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

mitchell

CA $101

CA $112 total

includes taxes & fees

Nov 23 - Nov 24

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

![Restaurant](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/fd85fd97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/a984ecc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/29d89638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/a19abecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Inn at Charles Town - Hollywood Casino

30 km from Old Town Winchester

8.6/10

Excellent

(504)

"Great place to stay to go to the casino"

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

Sandra

CA $164

CA $198 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.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)

![Lobby](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/c7da6581.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)

### Quality Inn Winchester

4.3 km from Old Town Winchester

9.2/10

Wonderful

(1001)

"All comments are very positive, staff, rooms, cleanliness, breakfast "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Lucie

CA $110

CA $119 total

includes taxes & fees

Nov 23 - Nov 24

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

![Individually furnished, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/d3f75196.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room amenity](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/aafb3606.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

12.4 km from Old Town Winchester

8.2/10

Very good

(786)

"Very friendly staff, clean, would definitely stay again "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Christie

CA $116

CA $126 total

includes taxes & fees

Nov 29 - Nov 30

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

![Property entrance](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/071235b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/a2451115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 10:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/f4004e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/c5b2135d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Baymont by Wyndham Front Royal Near Shenandoah National Park

29.8 km from Old Town Winchester

6.4/10

(907)

"Great staff"

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

Gordon

CA $77

CA $86 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Winchester-Hotels-Baymont-By-Wyndham-Front-Royal-Near-Shenandoah-National-Park.h10535.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)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/f063e2e9.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)

![View from property](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/fb0da257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites by Marriott Winchester

2.9 km from Old Town Winchester

9.0/10

Wonderful

(780)

"Super friendly staff, clean rooms, very convenient. I would definitely stay here again. "

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

Kathleen

CA $129

CA $141 total

includes taxes & fees

Nov 3 - Nov 4

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

![Premium bedding, pillowtop beds, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/73000000/72030000/72023600/72023562/fc21f98c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/73000000/72030000/72023600/72023562/w3000h1998x0y0-156eb7d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Laundry room](https://images.trvl-media.com/lodging/73000000/72030000/72023600/72023562/617e781a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free continental breakfast](https://images.trvl-media.com/lodging/73000000/72030000/72023600/72023562/c6b45b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Travelodge By Wyndham Charles Town/Harpers Ferry

29.5 km from Old Town Winchester

7.0/10

Good

(256)

"Wasn’t the cleanest but it’s good for a quick stop"

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

Autumn

CA $94

CA $106 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Charles-Town-Hotels-Travelodge-By-Wyndham-Charles-TownHarpers-Ferry.h72023562.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)

![Front of property](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/769f9c2b.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

2.1 km from Old Town Winchester

9.0/10

Wonderful

(1002)

"Staff was excellent !!! Hotel was clean and comfortable in great location !!! Would stay here again !!! "

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

Mary

CA $148

CA $167 total

includes taxes & fees

Nov 5 - Nov 6

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

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/4500/4419/9730f3d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/1000000/10000/4500/4419/f4aba607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4500/4419/913756e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/4500/4419/dfc64d18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Stephens City - Winchester South

12.4 km from Old Town Winchester

8.0/10

Very good

(617)

"Nice breakfast, clean room and friendly people."

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

Carrie

CA $110

CA $119 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Winchester-Hotels-Quality-Inn-Stephens-City-Winchester-South.h4419.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)

![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)

![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)

### Spark by Hilton Winchester

2 km from Old Town Winchester

9.0/10

Wonderful

(1003)

"Great location close to restaurants "

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

SILVIA

CA $121

CA $137 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.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/2000000/1500000/1497900/1497898/1b2ad59b.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)

### Courtyard by Marriott Winchester

3.1 km from Old Town Winchester

8.8/10

Excellent

(892)

"Nice, quiet, clean property in quaint town "

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

Jacqueline

CA $149

CA $162 total

includes taxes & fees

Nov 5 - Nov 6

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

![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1100000/1090600/1090593/326ab4b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1100000/1090600/1090593/424ee863.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)

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

3.1 km from Old Town Winchester

9.0/10

Wonderful

(792)

"Great place to stay!!"

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

Thomas

CA $167

CA $182 total

includes taxes & fees

Nov 28 - Nov 29

[](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Hotel-Suites-Winchester.h1090593.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=2025-11-13&endDate=2025-11-14&regionId=6164092&adults=2&sort=RECOMMENDED&openPlayBack=true)

## Hotels in Old Town Winchester with free breakfast

![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)

![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)

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

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

Old Town Winchester

-   Breakfast included
    

9.4/10

Exceptional

(1005)

CA $177

CA $200 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-06&endDate=2025-11-07&selected=1364026&PinnedHotelID=1364026&HadPinnedHotel=true&regionId=6164092&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663.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)

![1 bedroom, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/6a37f73c.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

7.8 km from Old Town Winchester

-   Breakfast included
    

9.4/10

Exceptional

(1049)

CA $141

CA $153 total

includes taxes & fees

Nov 1 - Nov 2

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-01&endDate=2025-11-02&selected=57958244&PinnedHotelID=57958244&HadPinnedHotel=true&regionId=6164092&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb.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)

![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)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/b1a55fc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Quinta Inn & Suites by Wyndham Winchester

2.9 km from Old Town Winchester

-   Breakfast included
    

9.2/10

Wonderful

(2189)

CA $143

CA $156 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true&regionId=6164092&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657.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)

![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/5447905f.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)

### Microtel Inn & Suites by Wyndham Winchester

4.1 km from Old Town Winchester

-   Breakfast included
    

9.2/10

Wonderful

(1351)

CA $109

CA $119 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=70921061&PinnedHotelID=70921061&HadPinnedHotel=true&regionId=6164092&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

![Snack bar](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b.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)

![Lobby](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/76fedaf8.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

4.4 km from Old Town Winchester

-   Breakfast included
    

9.0/10

Wonderful

(737)

CA $123

CA $134 total

includes taxes & fees

Nov 26 - Nov 27

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-26&endDate=2025-11-27&selected=39493421&PinnedHotelID=39493421&HadPinnedHotel=true&regionId=6164092&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

![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)

![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/57a6dfe3.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

5.3 km from Old Town Winchester

-   Breakfast included
    

9.4/10

Exceptional

(753)

CA $156

CA $169 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=42543772&PinnedHotelID=42543772&HadPinnedHotel=true&regionId=6164092&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde.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)

![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/0f2ede5e.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)

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

7.5 km from Old Town Winchester

-   Breakfast included
    

8.8/10

Excellent

(1002)

CA $127

CA $138 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=1652833&PinnedHotelID=1652833&HadPinnedHotel=true&regionId=6164092&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

![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

25 km from Old Town Winchester

-   Breakfast included
    

9.0/10

Wonderful

(1028)

CA $149

CA $165 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-09&endDate=2025-11-10&selected=892585&PinnedHotelID=892585&HadPinnedHotel=true&regionId=6164092&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2.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)

![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)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/ee4df7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

3.2 km from Old Town Winchester

-   Breakfast included
    

9.0/10

Wonderful

(1000)

CA $103

CA $116 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-30&endDate=2025-12-01&selected=1889084&PinnedHotelID=1889084&HadPinnedHotel=true&regionId=6164092&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

![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)

![Lobby](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/be9a8325.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)

### Ramada by Wyndham Strasburg/Shenandoah Valley

25.8 km from Old Town Winchester

-   Breakfast included
    

8.2/10

Very good

(1001)

CA $101

CA $112 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=1246311&PinnedHotelID=1246311&HadPinnedHotel=true&regionId=6164092&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true)

[See more properties](https://www.expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&regionId=6164092&adults=2&sort=RECOMMENDED&mealPlan=FREE_BREAKFAST&openPlayBack=true)

## Hotels in Old Town Winchester with a pool

![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/2000000/1500000/1497900/1497898/1b2ad59b.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)

### Courtyard by Marriott Winchester

3.1 km from Old Town Winchester

-   Pool
    

8.8/10

Excellent

(892)

CA $149

CA $162 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-05&endDate=2025-11-06&selected=1497898&PinnedHotelID=1497898&HadPinnedHotel=true&regionId=6164092&adults=2&amenities=POOL&openPlayBack=true)

![Property entrance](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/071235b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/a2451115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 10:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/f4004e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/c5b2135d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Baymont by Wyndham Front Royal Near Shenandoah National Park

29.8 km from Old Town Winchester

-   Pool
    

6.4/10

(907)

CA $77

CA $86 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-30&endDate=2025-12-01&selected=10535&PinnedHotelID=10535&HadPinnedHotel=true&regionId=6164092&adults=2&amenities=POOL&openPlayBack=true)

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

![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1100000/1090600/1090593/326ab4b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1100000/1090600/1090593/424ee863.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)

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

3.1 km from Old Town Winchester

-   Pool
    

9.0/10

Wonderful

(792)

CA $167

CA $182 total

includes taxes & fees

Nov 28 - Nov 29

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-28&endDate=2025-11-29&selected=1090593&PinnedHotelID=1090593&HadPinnedHotel=true&regionId=6164092&adults=2&amenities=POOL&openPlayBack=true)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/4500/4419/9730f3d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/1000000/10000/4500/4419/f4aba607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4500/4419/913756e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/4500/4419/dfc64d18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Stephens City - Winchester South

12.4 km from Old Town Winchester

-   Pool
    

8.0/10

Very good

(617)

CA $110

CA $119 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=4419&PinnedHotelID=4419&HadPinnedHotel=true&regionId=6164092&adults=2&amenities=POOL&openPlayBack=true)

[See more properties](https://www.expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&regionId=6164092&adults=2&sort=RECOMMENDED&amenities=POOL&openPlayBack=true)

## Top guest rated hotels in Old Town Winchester

![Courtyard](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/52d84062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![The Mary Rutherford Room](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/fead0911.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/6f99e56e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/a53cd216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Carriage Inn B&B

29.3 km from Old Town Winchester

9.6/10

Exceptional

(432)

CA $219

CA $248 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-06&endDate=2025-11-07&selected=2762649&PinnedHotelID=2762649&HadPinnedHotel=true&regionId=6164092&adults=2&guestRating=35&openPlayBack=true)

![Front of property - evening/night](https://images.trvl-media.com/lodging/12000000/11860000/11854200/11854156/bdaadecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 2 Double Beds, Non Smoking | View from room](https://images.trvl-media.com/lodging/12000000/11860000/11854200/11854156/182da075.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/12000000/11860000/11854200/11854156/eadb3a5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/12000000/11860000/11854200/11854156/a99c9843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relax Inn Motel

27.6 km from Old Town Winchester

8.2/10

Very good

(255)

CA $91

CA $101 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-30&endDate=2025-12-01&selected=11854156&PinnedHotelID=11854156&HadPinnedHotel=true&regionId=6164092&adults=2&guestRating=35&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/39d8617d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, soundproofing, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/08468627.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, soundproofing, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/2186fef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/030e20be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Twi-Lite Inn

27.8 km from Old Town Winchester

8.2/10

Very good

(532)

CA $86

CA $96 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-30&endDate=2025-12-01&selected=15799885&PinnedHotelID=15799885&HadPinnedHotel=true&regionId=6164092&adults=2&guestRating=35&openPlayBack=true)

![Restaurant](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/fd85fd97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/a984ecc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/29d89638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/a19abecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Inn at Charles Town - Hollywood Casino

30 km from Old Town Winchester

8.6/10

Excellent

(504)

CA $164

CA $198 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04&selected=76876848&PinnedHotelID=76876848&HadPinnedHotel=true&regionId=6164092&adults=2&guestRating=35&openPlayBack=true)

![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/8c81eb2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/a0a5a84e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/22bccc43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Renoir](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/ff749f7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### L'Auberge Provencale Inn & Restaurant

14.1 km from Old Town Winchester

9.6/10

Exceptional

(172)

CA $384

CA $424 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=15945622&PinnedHotelID=15945622&HadPinnedHotel=true&regionId=6164092&adults=2&guestRating=35&openPlayBack=true)

![Premium bedding, pillowtop beds, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/73000000/72030000/72023600/72023562/fc21f98c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/73000000/72030000/72023600/72023562/w3000h1998x0y0-156eb7d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Laundry room](https://images.trvl-media.com/lodging/73000000/72030000/72023600/72023562/617e781a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free continental breakfast](https://images.trvl-media.com/lodging/73000000/72030000/72023600/72023562/c6b45b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Travelodge By Wyndham Charles Town/Harpers Ferry

29.5 km from Old Town Winchester

7.0/10

Good

(256)

CA $94

CA $106 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=72023562&PinnedHotelID=72023562&HadPinnedHotel=true&regionId=6164092&adults=2&guestRating=35&openPlayBack=true)

![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)

![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)

![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)

![Reception](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745505/0ecd0e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### TownePlace Suites by Marriott Winchester

3 km from Old Town Winchester

8.8/10

Excellent

(468)

CA $149

CA $162 total

includes taxes & fees

Oct 31 - Nov 1

[](https://www.expedia.ca/Hotel-Search?startDate=2025-10-31&endDate=2025-11-01&selected=2745505&PinnedHotelID=2745505&HadPinnedHotel=true&regionId=6164092&adults=2&guestRating=35&openPlayBack=true)

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

![Lobby](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/037b096c.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)

### Hilton Garden Inn Winchester

2.1 km from Old Town Winchester

8.8/10

Excellent

(500)

CA $133

CA $151 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-09&endDate=2025-11-10&selected=2169428&PinnedHotelID=2169428&HadPinnedHotel=true&regionId=6164092&adults=2&guestRating=35&openPlayBack=true)

![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33120000/33110300/33110221/901f0183.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Single Room, 1 Queen Bed, Non Smoking | Private kitchen](https://images.trvl-media.com/lodging/34000000/33120000/33110300/33110221/63b9b0a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/34000000/33120000/33110300/33110221/4746b0aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33120000/33110300/33110221/c8e8c51c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ANS Inn & Suites

4 km from Old Town Winchester

7.6/10

Good

(65)

CA $85

CA $102 total

includes taxes & fees

Nov 20 - Nov 21

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-20&endDate=2025-11-21&selected=33110221&PinnedHotelID=33110221&HadPinnedHotel=true&regionId=6164092&adults=2&guestRating=35&openPlayBack=true)

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

![Front of property](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/769f9c2b.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

2.1 km from Old Town Winchester

9.0/10

Wonderful

(1002)

CA $148

CA $167 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-05&endDate=2025-11-06&selected=19971&PinnedHotelID=19971&HadPinnedHotel=true&regionId=6164092&adults=2&guestRating=35&openPlayBack=true)

[See more properties](https://www.expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&regionId=6164092&adults=2&sort=RECOMMENDED&guestRating=35&openPlayBack=true)

## Where to stay in Old Town Winchester

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

-   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=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 Winchester Little Theater.

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

## Top Old Town Winchester Hotel Reviews

![Super 8 by Wyndham Front Royal](//images.trvl-media.com/lodging/1000000/860000/855600/855557/10b5cc1e_y.jpg)

### Super 8 by Wyndham Front Royal

10/10 Excellent

"Clean room"

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

![Hampton Inn Winchester-University/Mall Area](//images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg)

### Hampton Inn Winchester-University/Mall Area

10/10 Excellent

"TV wasn’t in high definition. Could have been better."

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

![DoubleTree by Hilton Front Royal Blue Ridge Shadows](//images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a_y.jpg)

### DoubleTree by Hilton Front Royal Blue Ridge Shadows

10/10 Excellent

"The entire property was very clean and the staff extremely friendly."

[](https://expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information)

![Ramada by Wyndham Strasburg/Shenandoah Valley](//images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg)

### Ramada by Wyndham Strasburg/Shenandoah Valley

10/10 Excellent

"Not really a good breakfast area or food to choose from. The beds are hard the pillows are terrible plus the sheets had stains. The tvs are old and like only 5 channels to watch. Walls are thin "

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

![TRU By Hilton Winchester](//images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b_y.jpg)

### TRU By Hilton Winchester

10/10 Excellent

"Friendly staff, convenient location "

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

![Travelodge by Wyndham Winchester](//images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg)

### Travelodge by Wyndham Winchester

10/10 Excellent

"Stayed for a night on my way through town. Not a bad spot, clean and quiet. Staff was great. Lots of food delivery options around. "

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

![Days Inn by Wyndham Charles Town/Harpers Ferry](//images.trvl-media.com/lodging/11000000/10630000/10620700/10620696/6feea908_y.jpg)

### Days Inn by Wyndham Charles Town/Harpers Ferry

10/10 Excellent

"Did the job, cheap and cheerful, nothing to complain about! Good access to Harper’s Ferry"

[](https://expedia.ca/Martinsburg-Hotels-Days-Inn-By-Wyndham-Charles-TownHarpers-Ferry.h10620696.Hotel-Information)

![Hampton Inn Front Royal](//images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0_y.jpg)

### Hampton Inn Front Royal

10/10 Excellent

"We thoroughly enjoyed all aspects of our stay, and look forward to the next time."

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

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

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

10/10 Excellent

"Good"

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

## Find out more about Old Town Winchester

### Top reasons to visit Old Town Winchester

-   **Historic Landmarks:** Discover fascinating historic sites through guided walking tours that showcase Old Town Winchester's rich heritage.
-   **Charming Downtown:** Stroll through picturesque streets filled with quaint shops and delightful eateries, embodying the town's warm hospitality.
-   **Outdoor Adventures:** Enjoy recreational areas and scenic lakes, blending culture and nature for a perfect family-friendly experience.
-   **Diverse Accommodations:** Choose from a range of hotels, including pet-friendly and LGBTQIA welcoming options, ensuring comfort for all travellers.
-   **Weekend Getaways:** Immerse yourself in the scenic beauty of the surrounding regions, perfect for an unforgettable escape.

### Find great hotels near Old Town Winchester

Explore the charming hotel accommodations in Old Town Winchester, Virginia, where you can find a diverse range of options to suit every traveller's needs. Whether you're seeking pet-friendly lodgings, business-themed amenities, or LGBTQIA welcoming environments, this delightful area has something for everyone. Discover the best hotels, including Wyndham Winchester, and enjoy a memorable stay in a historic setting that beautifully blends modern comfort with timeless appeal.

-   **[Travelodge by Wyndham Winchester:](https://www.expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information)** A welcoming and convenient motel experience awaits at Travelodge by Wyndham Winchester, situated 3.2km from Old Town Winchester. This property is ideal for pet lovers, offering a pet-friendly atmosphere that ensures your furry companions can join in on the adventure. With essential amenities and a commitment to comfort, guests appreciate the straightforward lodging combined with the convenience of nearby attractions. The pet policy allows for both pets and service animals, ensuring a hassle-free stay for all.
-   **[La Quinta Inn & Suites by Wyndham Winchester:](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information)** Emphasizing a business-friendly environment, La Quinta Inn & Suites by Wyndham Winchester is just 3.2km from Old Town Winchester and welcomes both corporate and leisure travellers. This hotel stands out with its dedicated business centre and versatile meeting rooms, making it perfect for business trips or conferences. Additionally, it's a proud ally of the LGBTQIA community, creating an inclusive atmosphere for all guests. With a pet-friendly policy and modern amenities, this hotel successfully blends work and play.
-   **Red Roof Inn Winchester, VA:** Family-oriented and pet-friendly, Red Roof Inn Winchester, VA is an excellent choice for those travelling with children, located 3.2km from Old Town Winchester. The hotel features child-friendly amenities such as complimentary cribs, ensuring a comfortable stay for families. Additionally, as a supporter of the LGBTQIA community, it fosters an inclusive environment for all guests. The property's pet policy caters to both dogs and cats, making it easy for families to bring their beloved pets along for the journey.

### Where to stay near Old Town Winchester

Discover the charm of Old Town Winchester, where history meets hospitality. Stroll through the picturesque downtown, rich with historic attractions and family-friendly vibes. Enjoy Virginia's warm welcome as you explore quaint shops and delightful eateries. For a weekend getaway, immerse yourself in the scenic beauty of the surrounding regions, offering a perfect blend of urban and natural experiences. Old Town Winchester promises an unforgettable adventure for every traveller.

-   **[Winchester:](https://www.expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels)** Nestled in the heart of Virginia, Winchester is a vibrant city where Old Town Winchester serves as its historic nucleus. The city offers a year-round outdoor adventure experience, with scenic landscapes perfect for hiking and exploring. Popular activities include visiting nearby national parks and lakes, as well as enjoying skiing during the winter months. With a peak in visitor numbers during the summer and fall, Winchester is an excellent spot for those seeking both relaxation and adventure.
-   **[Winchester Historic District:](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels.0-n918789051029594112-0.Travel-Guide-Filter-Hotels)** Just 322m from Old Town Winchester, the Winchester Historic District is a charming neighborhood steeped in history. This area attracts families and outdoor enthusiasts alike, featuring golf courses and shopping centres. With its quaint parks and a welcoming visitor center, it's an ideal location to explore the unique blend of history and modern convenience. Expect a lively atmosphere, particularly during peak seasons in summer and autumn, making it a delightful stop for visitors looking for family-friendly activities.
-   **[College Park:](https://www.expedia.ca/College-Park-Hotels.d553248635975870482.Travel-Guide-Hotels)** Located 3.2km from Old Town Winchester, College Park is a quaint village that perfectly complements your travel itinerary. Known for its outdoor experiences, this area offers excellent recreational opportunities and winter sports, including skiing. The proximity to national parks and a marina makes it attractive for nature lovers and adventure seekers. With a steady flow of visitors throughout the year, College Park provides a laid-back atmosphere to unwind and enjoy the scenic beauty of Virginia.

### Things to do in and around Old Town Winchester

Old Town Winchester offers a delightful mix of outdoor and family-friendly activities. You can enjoy recreational areas and explore educational sites while shopping at the local centre. Don’t miss the chance to embark on guided walking tours through historic landmarks, providing a fascinating insight into the town's rich heritage. For a memorable experience, plan your trip around the charming streets of Old Town Winchester.

**Shopping**

In Old Town Winchester, you can find unique gifts at [Nalls Farm Market](https://www.expedia.ca/Nalls-Farm-Market-Hotels.0-l553248621532661846-0.Travel-Guide-Filter-Hotels), just 1.6km away. For a more extensive shopping experience, visit the Apple Valley Square Shopping Center and Eastgate Plaza Shopping Center, both offering a blend of local businesses and family-friendly vibes.

**Recreation**

[Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Hotels.0-l6164028-0.Travel-Guide-Filter-Hotels) offers a tranquil environment for relaxation and leisurely strolls, only 1.4km from Old Town Winchester. For those seeking outdoor activities, [Rock Harbor Golf Course](https://www.expedia.ca/Rock-Harbor-Golf-Course-Hotels.0-l553248621561864838-0.Travel-Guide-Filter-Hotels), 3.2km away, provides a vibrant atmosphere for golf enthusiasts. [Appleland Sports Center](https://www.expedia.ca/Appleland-Sports-Center-Hotels.0-l553248621587477489-0.Travel-Guide-Filter-Hotels), 9.7km distant, focuses on wellness and rejuvenation.

**Adventure**

Experience the thrill of racing at [Summit Point Motorsports Park](https://www.expedia.ca/Summit-Point-Motorsports-Park-Hotels.0-l6164103-0.Travel-Guide-Filter-Hotels), located 17.7km from Old Town Winchester, where adrenaline meets speed. For a family-friendly outdoor adventure, visit [Watermelon Park Campground](https://www.expedia.ca/Watermelon-Park-Campground-Hotels.0-l553248621532661928-0.Travel-Guide-Filter-Hotels), 20.9km away, offering camping and nature activities. Don’t miss hiking the scenic [Tuckers Lane Trailhead](https://www.expedia.ca/Tuckers-Lane-Trailhead-Hotels.0-l553248633992585760-0.Travel-Guide-Filter-Hotels), 32.2km distant.

**Nightlife**

Experience the vibrant nightlife of Old Town Winchester at [Bright Box Theater](https://www.expedia.ca/Bright-Box-Theater-Hotels.0-l553248621561864843-0.Travel-Guide-Filter-Hotels), where culture and entertainment come alive. For a unique touch, visit the nearby [Morgan County Observatory](https://www.expedia.ca/Morgan-County-Observatory-Hotels.0-l553248621558141373-0.Travel-Guide-Filter-Hotels) for stargazing. Don’t miss the [Winchester Little Theater](https://www.expedia.ca/Winchester-Little-Theater-Hotels.0-l6164047-0.Travel-Guide-Filter-Hotels), perfect for a romantic evening filled with artistic charm.

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

### Booking tips and Expedia advantages for Old Town Winchester

To save money on your vacation to Old Town Winchester, consider visiting between January and March for lower accommodation rates. Tuesdays are typically the least expensive days to stay, while Saturdays are the priciest. Use Expedia to find deals by filtering for budget-friendly options and eco-certified hotels. Combining your hotel, flights, and activities into a package can also lead to significant savings. Take advantage of free local attractions and explore the town on foot to minimize transport costs.

-   **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay around Old Town 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 around Old Town Winchester is Tuesday. The most expensive day to stay around Old Town Winchester is Saturday.
-   **Find cheap hotels on Expedia:** Utilize Expedia's search tool to refine your preferences, such as your budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly accommodations currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
-   **Consider bundling your trip:** You can save money by combining your hotel stay in Old Town Winchester with your flights and activities through an Expedia package.

### Find the best attractions in and around Old Town Winchester

Old Town Winchester offers a delightful mix of outdoor adventures and family-friendly experiences, with attractions such as the historic downtown area and the scenic Winchester Historic District. Visitors can explore the charming historic houses and enjoy the nearby lakes, providing a perfect blend of culture and nature. Don't miss out on discovering the best attractions in Winchester, where history and outdoor fun come together beautifully for an unforgettable vacation.

-   **[Shenandoah University:](https://www.expedia.ca/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels)** This historic university, located 1.6km from Old Town Winchester, offers visitors a glimpse of vibrant campus life and beautiful architecture. Experience the cultural vibes through its various events and performances.
-   **[Museum of the Shenandoah Valley:](https://www.expedia.ca/Museum-Of-The-Shenandoah-Valley-Hotels.0-l6127313-0.Travel-Guide-Filter-Hotels)** Situated 1.3km away, this art museum showcases regional art and history, providing a rich cultural experience. Explore its stunning galleries and beautiful gardens, perfect for a leisurely stroll.
-   **[Shenandoah Valley Discovery Museum:](https://www.expedia.ca/Shenandoah-Valley-Discovery-Museum-Hotels.0-l553248621587527659-0.Travel-Guide-Filter-Hotels)** Located within Old Town Winchester, this children's museum is a delightful space for families. With interactive exhibits, it encourages learning through play, making it a wonderful destination for kids and parents alike.

### Best time to go to Old Town Winchester

The best time to visit Old Town 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 Old Town Winchester

For your visit to Old Town Winchester, you can fly into several nearby airports. 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, with nearby hotels like the 4-star [Hyatt Regency Dulles](https://www.expedia.ca/Herndon-Hotels-Hyatt-Regency-Dulles.h150.Hotel-Information), just 1.6km from the airport. Hagerstown Regional Airport ([HGR](https://www.expedia.ca/Hagerstown-Regional-Airport-Hotels.0-aHGR-0.Travel-Guide-Filter-Hotels)), located 69.2km away, offers options such as the 4-star Mercersburg Inn, 19.3km from the airport. The closest is Eastern West Virginia Regional Airport (MRB), situated 29.0km away, with accommodations like the 4-star [Hillbrook Inn](https://www.expedia.ca/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information), 11.6kms from the airport. Each airport provides accessible transportation options to ensure a smooth journey to Old Town Winchester.

## Frequently asked questions

### What are the best hotels in Old Town Winchester that travellers recommend?

> [The George Washington Hotel, A Wyndham Grand Hotel](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information), is a highly praised destination in Old Town Winchester, boasting a great rating of 9.4. This Georgian-style property offers a luxurious retreat with a full-service spa, superb for those looking to unwind after a day of adventure. Guests rave about the onsite massage services and the option for in-room pampering, ensuring a relaxing stay.

### What are the best family hotels in Old Town Winchester?

> [The George Washington Hotel, A Wyndham Grand Hotel](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information), stands out as an exceptional choice for families visiting Old Town Winchester, boasting an impressive traveller review score of 9.4. This hotel not only offers connecting rooms, making it convenient for families to stay close together, but also provides free cribs for little ones, ensuring a comfortable stay for guests of all ages.

### What are the best spa hotels in Old Town Winchester?

> For a rejuvenating escape, [The George Washington Hotel, A Wyndham Grand Hotel](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) is a great choice in Old Town Winchester, boasting an impressive customer review rating of 9.4. This historic hotel features a full-service spa where guests can indulge in a range of treatments, including in-room massages, ensuring a personalized and relaxing experience.

### What are the best budget hotels in Old Town Winchester?

> [The George Washington Hotel, A Wyndham Grand Hotel](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information), is a fantastic option for travellers seeking comfort and convenience in Old Town Winchester. With a stellar review rating of 9.4, this hotel effortlessly combines modern amenities with a touch of historic charm.

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

> You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Old Town Winchester.

### How can I save on a Old Town Winchester hotel booking with Expedia?

> Members always get our best prices. Find our best Old Town Winchester hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.

### How much is the nightly rate at a Old Town Winchester hotel?

> Hotel prices in Old Town Winchester often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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-   [Hotels near Winchester Medical Center](https://www.expedia.ca/Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels)
-   [Motels in Winchester](https://www.expedia.ca/Winchester-Motels.d6056879-aaMotels.Travel-Guide-Accommodation)

-   [Flights to Boyce](https://www.expedia.ca/Cheap-Flights-To-Boyce.d184084.Travel-Guide-Flights)
-   [Flights to Winchester](https://www.expedia.ca/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)
-   [Flights from Winchester Regional](https://www.expedia.ca/lp/airports/wgo/flights-from-winchester-regional-airport)
-   [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)
-   [Winchester Vacations](https://www.expedia.ca/Winchester.d6056879.Destination-Travel-Guides)

-   [Budget Rental Cars in Winchester](https://www.expedia.ca/Budget-Car-Rentals-In-Winchester.d6056879-c39.Car-Rental-Guide-Suppliers)
-   [Car rental Winchester](https://www.expedia.ca/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide)
-   [National Car Rental Rental Cars in Winchester](https://www.expedia.ca/National-Car-Rental-Car-Rentals-In-Winchester.d6056879-c42.Car-Rental-Guide-Suppliers)

-   [Winchester Vacation Rentals](https://www.expedia.ca/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)

-   [Things to do in Winchester](https://www.expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)

-   [Book Hotels in Old Town Winchester on Expedia.com](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels)