Title: Book The Best Hotels in Upperville, VA for 2025 from CA $96 - Competitive Prices - Expedia.ca

 

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Photo by Michael Gibson

# Find hotels in Upperville, VA from CA $96

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## Go beyond your typical stay in Upperville

Spa

[](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-11-27&d1=2025-11-27&endDate=2025-11-29&d2=2025-11-29&amenities=SPA_ON_SITE)

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-11-27&d1=2025-11-27&endDate=2025-11-29&d2=2025-11-29&travelerType=family_friendly)

Hot tub

[](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-11-27&d1=2025-11-27&endDate=2025-11-29&d2=2025-11-29&amenities=HOT_TUB)

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-11-27&d1=2025-11-27&endDate=2025-11-29&d2=2025-11-29&amenities=POOL)

Apart­ment

[](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-11-27&d1=2025-11-27&endDate=2025-11-29&d2=2025-11-29&lodging=APARTMENT)

Cottage

[](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-11-27&d1=2025-11-27&endDate=2025-11-29&d2=2025-11-29&lodging=COTTAGE)

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America&regionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-11-27&d1=2025-11-27&endDate=2025-11-29&d2=2025-11-29&amenities=PETS)

## Check prices for these dates

Tonight

[Nov 13 - Nov 14](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-11-13&endDate=2025-11-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 14 - Nov 15](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-11-14&endDate=2025-11-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Compare 719 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

![Indoor pool](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/a9078e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/1054ff00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/627db10f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/cba53522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Clarion Inn Harpers Ferry - Charles Town

Harpers Ferry

7.8/10

Good

(1001)

"Great staff. Great location. Great restaurant "

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

bradley

CA $125

CA $140 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Martinsburg-Hotels-Clarion-Inn-Harpers-Ferry-Charles-Town.h977326.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/21ca3455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/8a0b17e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Couples treatment rooms, sauna, hot tub, steam room, hot springs](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/43873b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 restaurants, breakfast, lunch, dinner served; local cuisine](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/b8f43b35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Salamander Resort And Spa

Middleburg

9.2/10

Wonderful

(369)

"The property is at a close proximity to the downtown area. We were able to walk everywhere. Our room was spacious and immaculate. "

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

Cedric

CA $736

CA $911 total

includes taxes & fees

Nov 17 - Nov 18

[](https://www.expedia.ca/Middleburg-Hotels-Salamander-Resort-And-Spa.h6022232.Hotel-Information)

![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)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/bff9ad76.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)

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

Old Town Winchester

9.4/10

Exceptional

(1006)

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

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

Casey

CA $177

CA $201 total

includes taxes & fees

Nov 20 - Nov 21

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

![Rooftop terrace](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/89e72fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/202ce6ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/430b62d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/8910bd36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Charles Town by IHG

Charles Town

9.2/10

Wonderful

(1001)

"Great stay "

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

Gwinn

CA $156

CA $176 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Martinsburg-Hotels-Holiday-Inn-Express-Charles-Town.h1554858.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73570000/73560200/73560131/79fcba7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/74000000/73570000/73560200/73560131/0d6997c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 King Bed, City View | City view](https://images.trvl-media.com/lodging/74000000/73570000/73560200/73560131/20a3d6ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/74000000/73570000/73560200/73560131/07cd4f83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Haymarket

Haymarket

9.4/10

Exceptional

(243)

"Comfortable rooms, clean hallways and lobby.Overall a great property."

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

sukriti

CA $173

CA $200 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Haymarket-Hotels-Hilton-Garden-Inn-Haymarket.h73560131.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)

![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)

![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

(2207)

"One of the nicest places we’ve stayed "

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

Robert

CA $146

CA $159 total

includes taxes & fees

Dec 14 - Dec 15

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

![Reception](https://images.trvl-media.com/lodging/5000000/4540000/4532700/4532660/4441f7ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![32-inch LCD TV with satellite channels, TV](https://images.trvl-media.com/lodging/5000000/4540000/4532700/4532660/26679b2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4540000/4532700/4532660/ad3e0e1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/5000000/4540000/4532700/4532660/39c165a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn & Suites Charles Town

Charles Town

9.4/10

Exceptional

(1001)

"The staff was extremely friendly and respectful. "

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

Thomas

CA $156

CA $174 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Martinsburg-Hotels-Hampton-Inn-Suites-Charles-Town.h4532660.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)

![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)

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

### TRU By Hilton Winchester

Winchester

9.0/10

Wonderful

(754)

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

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

Sherri

CA $111

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/2000000/1830000/1828900/1828858/de680848.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1830000/1828900/1828858/15468136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1830000/1828900/1828858/fbfa3983.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1830000/1828900/1828858/2fb5a2e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn by Hilton Gainesville-Haymarket

Gainesville

8.8/10

Excellent

(972)

"Right next to some great dining and bar options "

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

Ryan

CA $118

CA $134 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Gainesville-Hotels-Hampton-Inn-By-Hilton-Gainesville-Haymarket.h1828858.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/1000000/20000/10100/10086/ad87d83f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10100/10086/01bb26bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/1000000/20000/10100/10086/5d8b5ff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio Suite, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/10100/10086/af8ba0cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Baymont by Wyndham Warrenton

Warrenton

6.4/10

(1001)

"Room was clean. Breakfast was great. Easy parking."

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

Brian

CA $97

CA $104 total

includes taxes & fees

Nov 20 - Nov 21

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

![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/3000000/2940000/2933800/2933741/6a58d545.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2940000/2933800/2933741/5aa6585c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Studio, Non Smoking, Refrigerator & Microwave](https://images.trvl-media.com/lodging/3000000/2940000/2933800/2933741/671381db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Studio, Non Smoking, Refrigerator & Microwave](https://images.trvl-media.com/lodging/3000000/2940000/2933800/2933741/c1ac9b70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Extended Stay America Select Suites Gainesville

Gainesville

6.2/10

(475)

"Amazing place "

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

Evelyn

CA $99

CA $113 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Gainesville-Hotels-WoodSpring-Suites-Gainesville-VA.h2933741.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)

![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

(502)

"Good stay"

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

Keishun

CA $134

CA $152 total

includes taxes & fees

Nov 23 - Nov 24

[](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)

![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)

![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

(1002)

"Clean, nice breaksfast service"

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

George

CA $98

CA $111 total

includes taxes & fees

Nov 16 - Nov 17

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

![Individually furnished, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/fcd1c267.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)

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

Stephens City

8.2/10

Very good

(793)

"The front desk did a great job with checking in and out."

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

Eric

CA $122

CA $133 total

includes taxes & fees

Nov 21 - Nov 22

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

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9925792b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/1487a76c.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/1000000/10000/9600/9600/7d84d9df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/11fe2bc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Travelodge by Wyndham Winchester

Winchester

8.6/10

Excellent

(1089)

"It's been a great stay so far"

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

Sabrina

CA $98

CA $107 total

includes taxes & fees

Dec 14 - Dec 15

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

![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)

![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/3c75b4dc.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)

### Candlewood Suites Winchester by IHG

Winchester

8.8/10

Excellent

(534)

"Very clean room, excellent staff!!!"

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

James

CA $125

CA $136 total

includes taxes & fees

Nov 30 - Dec 1

[](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)

![Exterior](https://images.trvl-media.com/lodging/1000000/860000/856400/856310/78b01efc.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)

### Econo Lodge Inn & Suites

Middletown

5.8/10

(297)

"Clean room"

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

Judy

CA $87

CA $96 total

includes taxes & fees

Nov 20 - Nov 21

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

![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32440000/32431200/32431174/6cb6a218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Middleburg Cottage | Living area](https://images.trvl-media.com/lodging/33000000/32440000/32431200/32431174/f6f51ac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Middleburg Cottage](https://images.trvl-media.com/lodging/33000000/32440000/32431200/32431174/06ac9573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/33000000/32440000/32431200/32431174/56e9357e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Red Fox Inn & Tavern

Middleburg

9.6/10

Exceptional

(399)

"Wonderful stay. So much history! It is so cool to think that you are in a 300 year old inn that has served countless travelers."

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

Neal

[](https://www.expedia.ca/Middleburg-Hotels-The-Red-Fox-Inn-Tavern.h32431174.Hotel-Information)

![Premium bedding, down comforters, in-room safe, individually decorated](https://images.trvl-media.com/lodging/2000000/1370000/1360400/1360309/e6e66ad4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/2000000/1370000/1360400/1360309/c0f63216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1370000/1360400/1360309/4b804569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 restaurants, breakfast, lunch served; local and international cuisine](https://images.trvl-media.com/lodging/2000000/1370000/1360400/1360309/fb2943f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Goodstone Inn & Restaurant

Middleburg

9.6/10

Exceptional

(47)

"Absolutely beautiful property, Virginia Countryside at its finest. A wonderful retreat from modern day life."

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

Johan Oliver

CA $531

CA $730 total

includes taxes & fees

Nov 18 - Nov 19

[](https://www.expedia.ca/Middleburg-Hotels-Goodstone-Inn-Restaurant.h1360309.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)

![Front of property](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/6a9fc093.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)

### The Inn at Charles Town - Hollywood Casino

Charles Town

8.6/10

Excellent

(508)

"Fun trip "

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

Arthur

CA $217

CA $258 total

includes taxes & fees

Nov 21 - Nov 22

[](https://www.expedia.ca/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.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=2025-11-27&endDate=2025-11-28&regionId=184116&adults=2&sort=RECOMMENDED&openPlayBack=true)

![](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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## Learn more about Upperville

Hunt country elegance shines at the historic Upperville Horse Show, America's oldest running exhibition where equestrians compete each June. Wander through the quaint village to discover stone buildings, antique shops, and Sky Meadows State Park's hiking trails nearby in Paris.

[See all hotels in Upperville](https://www.expedia.ca/Hotel-Search?startDate=2025-11-27&endDate=2025-11-28&adults=2&regionId=184116)

![Hiking Sky Meadows State Park...](https://images.trvl-media.com/place/553248621532661864/008a9705-5d69-4bff-87e9-dd23f82e56ed.jpg?impolicy=fcrop&w=899&h=675&p=1&q=high)

Photo by Michael Gibson

## More cheap stays in Upperville

![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Hampton Inn Winchester-University/Mall Area

640 East Jubal Early Drive, Winchester, VA

CA $145

CA $164 total

Nov 20 - Nov 21

includes taxes & fees

9/10 Wonderful! (1,001 reviews)

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

![Clarion Hotel & Conference Center Leesburg](https://images.trvl-media.com/lodging/1000000/30000/24400/24372/8c4e2827_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Clarion Hotel & Conference Center Leesburg

1500 E Market St, Leesburg, VA

CA $125

CA $144 total

Nov 30 - Dec 1

includes taxes & fees

6.6/10 (1,002 reviews)

[](https://expedia.ca/Leesburg-Hotels-Clarion-Hotel-Conference-Center-Leesburg.h24372.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 $142

CA $154 total

Nov 21 - Nov 22

includes taxes & fees

9.4/10 Exceptional! (1,048 reviews)

[](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.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, U.S. 29, Warrenton, VA

CA $97

CA $104 total

Nov 20 - Nov 21

includes taxes & fees

6.4/10 (1,004 reviews)

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

![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Travelodge by Wyndham Winchester

160 Front Royal Pike, Winchester, VA

CA $98

CA $107 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)

![Red Roof Inn Leesburg, VA](https://images.trvl-media.com/lodging/1000000/20000/17600/17577/610f0a4e_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Red Roof Inn Leesburg, VA

721 East Market Street, Leesburg, VA

CA $115

CA $132 total

Nov 23 - Nov 24

includes taxes & fees

8.4/10 Very Good! (1,006 reviews)

[](https://expedia.ca/Leesburg-Hotels-Red-Roof-Inn-Leesburg.h17577.Hotel-Information)

## Hotels in Upperville with star-rating

![5 Star Hotels](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/21ca3455_w.jpg)

5 Star Hotels

2 properties

[](https://expedia.ca/5Star-Upperville-Hotels.s50-0-d184116.Travel-Guide-Filter-Hotels)

![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/27700/27700/5ae32850_w.jpg)

4 Star Hotels

12 properties

[](https://expedia.ca/4Star-Upperville-Hotels.s40-0-d184116.Travel-Guide-Filter-Hotels)

![3 Star Hotels](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_w.jpg)

3 Star Hotels

94 properties

[](https://expedia.ca/3Star-Upperville-Hotels.s30-0-d184116.Travel-Guide-Filter-Hotels)

![2 Star Hotels](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_w.jpg)

2 Star Hotels

109 properties

[](https://expedia.ca/2Star-Upperville-Hotels.s20-0-d184116.Travel-Guide-Filter-Hotels)

## Recent reviews of Upperville hotels

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

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

5/5 Excellent

"Yes great hotel!!"

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

Posted 1 day ago

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

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

### La Quinta Inn & Suites by Wyndham Winchester

5/5 Excellent

"Nice place "

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

Posted 2 days ago

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

![Comfort Inn & Suites Winchester](//images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg)

### Comfort Inn & Suites Winchester

5/5 Excellent

"Nice room clean staff very nice "

A verified traveller stayed at Comfort Inn & Suites Winchester

Posted 2 days ago

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

![Holiday Inn Express Charles Town by IHG](//images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/89e72fbd_y.jpg)

### Holiday Inn Express Charles Town by IHG

5/5 Excellent

"The staff was very courteous with asssiting us with a crib for our baby and ensuring we were placed in a room near the elevator. The room was very spacious for our family of 5"

A verified traveller stayed at Holiday Inn Express Charles Town by IHG

Posted 5 days ago

[](https://expedia.ca/Martinsburg-Hotels-Holiday-Inn-Express-Charles-Town.h1554858.Hotel-Information)

![Microtel Inn & Suites by Wyndham Winchester](//images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg)

### Microtel Inn & Suites by Wyndham Winchester

5/5 Excellent

"Excellent accommodations"

A verified traveller stayed at Microtel Inn & Suites by Wyndham Winchester

Posted 6 days ago

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

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

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

5/5 Excellent

"Good"

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

Posted 6 days ago

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

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

### Hampton Inn Front Royal

5/5 Excellent

"Everything was Great! Friendly Staff."

A verified traveller stayed at Hampton Inn Front Royal

Posted 6 days ago

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

![Hampton Inn & Suites Charles Town](//images.trvl-media.com/lodging/5000000/4540000/4532700/4532660/4441f7ed_y.jpg)

### Hampton Inn & Suites Charles Town

5/5 Excellent

"The front desk staff was just wonderful. I think, Julie(??), deserve a shout out. "

A verified traveller stayed at Hampton Inn & Suites Charles Town

Posted 7 days ago

[](https://expedia.ca/Martinsburg-Hotels-Hampton-Inn-Suites-Charles-Town.h4532660.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

5/5 Excellent

"Friendly staff"

A verified traveller stayed at DoubleTree by Hilton Front Royal Blue Ridge Shadows

Posted 7 days ago

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

## Frequently asked questions

### How much does a pet-friendly hotel in Upperville cost?

> You can find pet-friendly hotels in Upperville from CA $96 with Expedia. Staying at a pet-friendly hotel offers a convenient and welcoming experience for travellers who don't want to leave their furry companions behind. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

### Which area of Upperville is best to stay in for pet-friendly hotels?

> The best area to stay in Upperville for pet-friendly hotels is the immediate vicinity of the village centre, particularly along John S. Mosby Highway (Route 50).
> 
>   
> 
> This area is the heart of Upperville, where you'll find the primary cluster of accommodations. It's characterised by its equestrian heritage, with many properties offering a relaxed, country feel. You'll find a few local shops and eateries here, making it a convenient base.
> 
>   
> 
> Couples travelling with their pets will find this area particularly suitable. Many of the inns and guesthouses here understand the needs of pet owners, often providing amenities like designated walking areas or even special treats for furry companions. The surrounding countryside offers ample opportunities for long walks with your dog.
> 
>   
> 
> For solo travellers bringing a pet, staying near the village centre provides easy access to dining options and local points of interest without needing to drive far.

### How do I ensure I have booked a pet-friendly room in Upperville?

> To ensure you've booked a pet-friendly room on Expedia, use the filters in your search and select "Pet friendly" under the "Amenities" section. This will narrow your options to properties that allow pets. Once you find a hotel you're interested in, click on it and review the "Policies" section for specific details about their pet policy. This often includes information about pet types, size restrictions, fees, and whether pets are allowed in all rooms or only certain ones.When selecting your room type, read the room description to check that its pet-friendly, as not all rooms in a pet-friendly hotel may accommodate pets. For added peace of mind, contact the hotel directly to confirm the room you've selected allows pets.

### What pet-friendly activities should we do in Upperville?

> The best areas to stay in Upperville are generally around the village centre for convenience or slightly outside for a more secluded, rural experience.
> 
>   
> 
> The village centre of Upperville itself is quite small and historic, primarily focused around the intersection of Main Street (Route 50) and Delaplane Grade Road. You'll find a few charming inns and guest houses here, often within walking distance of the local shops and the historic Trinity Episcopal Church. This area provides easy access to the local equestrian scene and community events.
> 
>   
> 
> For couples looking for a romantic and quiet escape, staying in one of the boutique inns or bed and breakfasts just outside the village centre is ideal. These properties often feature expansive grounds, offering privacy and scenic views of the rolling Virginia countryside. Many offer amenities like private patios or fireplaces, great for a relaxing getaway.
> 
>   
> 
> Families might prefer properties that are slightly larger, perhaps a guesthouse or a holiday rental with more space, often found a little further out from the immediate village centre. These accommodations can provide more room for children to play and often have facilities like kitchens, which are convenient for preparing meals.

### What amenities should I look for in a pet-friendly hotel in Upperville?

> When selecting a hotel in Upperville for you and your pet, look for amenities like food and water bowls, pet-friendly outdoor spaces and pet beds. You may find hotels that go the extra mile with pet-friendly dining options, treats and toys. It's also worth looking to see if there are any pet-friendly parks or walking trails nearby.

### How can I save on a pet-friendly hotel in Upperville with Expedia?

> There are plenty of ways to save on a pet-friendly hotel in Upperville. Join [One Key™](https://www.expedia.ca/welcome-one-key)—Expedia's free travel rewards program—to unlock discounted Member Prices. Typically, booking in advance will help you save on your pet-friendly hotel booking.

### Do any Upperville hotels have restrictions on pet sizes or breeds?

> First ensure you have picked a pet-friendly hotel by using the "Pet friendly" filter under the "Amenities" section in your search. If a hotel in Upperville has restrictions on pet sizes or breeds, you will find this information clearly in their property listing on Expedia. When you're on the property listing page, simply click on "Policies" to see what pet-specific policies the hotel implements.

### Is it cheaper to book flights and a pet-friendly hotel in Upperville 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.

### Can I cancel my pet-friendly 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 pet-friendly hotel in Upperville for you.

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-   [Farmstay in Paris](https://www.expedia.ca/Paris-Agritourism.d6050691-aaAgritourism.Travel-Guide-Accommodation)
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-   [Paris Hotels](https://www.expedia.ca/Paris-Hotels.d6050691.Travel-Guide-Hotels)
-   [Inns in Paris](https://www.expedia.ca/Paris-Inns.d6050691-aaInns.Travel-Guide-Accommodation)
-   [Motels in Paris](https://www.expedia.ca/Paris-Motels.d6050691-aaMotels.Travel-Guide-Accommodation)
-   [Resorts in Paris](https://www.expedia.ca/Paris-Resort-Hotels.d6050691-aaResortHotels.Travel-Guide-Accommodation)
-   [Purcellville Hotels](https://www.expedia.ca/Purcellville-Hotels.d6338641.Travel-Guide-Hotels)
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-   [Round Hill Hotels](https://www.expedia.ca/Round-Hill-Hotels.d3000460647.Travel-Guide-Hotels)
-   [Hotels near Sky Meadows State Park](https://www.expedia.ca/Sky-Meadows-State-Park-Hotels.0-l553248621532661864-0.Travel-Guide-Filter-Hotels)
-   [Hotels near State Arboretum of Virginia](https://www.expedia.ca/State-Arboretum-Of-Virginia-Hotels.0-l6164038-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Stone Tower Winery](https://www.expedia.ca/Stone-Tower-Winery-Hotels.0-l553248633992315417-0.Travel-Guide-Filter-Hotels)
-   [The Plains Hotels](https://www.expedia.ca/The-Plains-Hotels.d3000460694.Travel-Guide-Hotels)
-   [Hotels near Watermelon Park Campground](https://www.expedia.ca/Watermelon-Park-Campground-Hotels.0-l553248621532661928-0.Travel-Guide-Filter-Hotels)
-   [White Post Hotels](https://www.expedia.ca/White-Post-Hotels.d184119.Travel-Guide-Hotels)

-   [Flights to Paris](https://www.expedia.ca/Cheap-Flights-To-Paris.d6050691.Travel-Guide-Flights)
-   [Flights from Markham](https://www.expedia.ca/lp/flights/553248635975848092/flights-from-markham)
-   [Flights from Middleburg](https://www.expedia.ca/lp/flights/55837/flights-from-middleburg)

-   [Naked Mountain Winery & Vineyards](https://www.expedia.ca/Naked-Mountain-Winery-Vineyards-Delaplane.d553248621532661859.Vacation-Attraction)

-   [Car rental Middleburg](https://www.expedia.ca/Car-Rentals-In-Middleburg.d55837.Car-Rental-Guide)
-   [Car rental Paris](https://www.expedia.ca/Car-Rentals-In-Paris.d6050691.Car-Rental-Guide)

-   [Things to do in Bluemont](https://www.expedia.ca/Things-To-Do-In-Bluemont.d6348602.Travel-Guide-Activities)
-   [Things to do in Middleburg](https://www.expedia.ca/Things-To-Do-In-Middleburg.d55837.Travel-Guide-Activities)

-   [Book Hotels in Upperville on Expedia.com](https://www.expedia.com/Upperville-Hotels.d184116.Travel-Guide-Hotels)

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