Title: Book The Best Hotels in Upperville, VA for 2025 from CA $102 - Fully Refundable Options - Expedia.ca [Vacation Rentals in Upperville](https://expedia.ca/Upperville-Vacation-Rentals.d184116.Travel-Guide-VacationRentals)[Upperville Car Rentals](https://expedia.ca/Car-Rentals-In-Upperville.d184116.Car-Rental-Guide)[Upperville Vacation Packages](https://expedia.ca/Upperville.d184116.Destination-Travel-Guides) ![Hiking Sky Meadows State Park...](https://images.trvl-media.com/place/553248621532661864/008a9705-5d69-4bff-87e9-dd23f82e56ed.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Michael Gibson # Find hotels in Upperville, VA from CA $102 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Upperville Spa [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-12-11&d1=2025-12-11&endDate=2025-12-13&d2=2025-12-13&amenities=SPA_ON_SITE) Cabin [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-12-11&d1=2025-12-11&endDate=2025-12-13&d2=2025-12-13&lodging=CABIN) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-12-11&d1=2025-12-11&endDate=2025-12-13&d2=2025-12-13&travelerType=family_friendly) Pool [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-12-11&d1=2025-12-11&endDate=2025-12-13&d2=2025-12-13&amenities=POOL) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-12-11&d1=2025-12-11&endDate=2025-12-13&d2=2025-12-13&amenities=HOT_TUB) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-12-11&d1=2025-12-11&endDate=2025-12-13&d2=2025-12-13&lodging=APARTMENT) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-12-11&d1=2025-12-11&endDate=2025-12-13&d2=2025-12-13&lodging=COTTAGE) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-12-11&d1=2025-12-11&endDate=2025-12-13&d2=2025-12-13&amenities=PETS) Chalet [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-12-11&d1=2025-12-11&endDate=2025-12-13&d2=2025-12-13&lodging=CHALET) Waterpark [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-12-11&d1=2025-12-11&endDate=2025-12-13&d2=2025-12-13&amenities=WATER_PARK) Farm [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-12-11&d1=2025-12-11&endDate=2025-12-13&d2=2025-12-13&lodging=AGRITOURISM) ## Check prices for these dates Tonight [Nov 27 - Nov 28](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-11-27&endDate=2025-11-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 28 - Nov 29](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-11-28&endDate=2025-11-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Compare 722 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable. ![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) ![View from room](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/e6b54e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salamander Resort And Spa Middleburg 9.2/10 Wonderful (370) "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 $772 CA $953 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Middleburg-Hotels-Salamander-Resort-And-Spa.h6022232.Hotel-Information) ![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) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/75fa7cd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clarion Inn Harpers Ferry - Charles Town Harpers Ferry 7.8/10 Good (1009) "Nice convenient hotel. Clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason CA $125 CA $140 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Martinsburg-Hotels-Clarion-Inn-Harpers-Ferry-Charles-Town.h977326.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/74000000/73570000/73560200/73560131/671c5bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Haymarket Haymarket 9.4/10 Exceptional (247) "This hotel is clean with a restaurant and a bar, staff is friendly and kind " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marita CA $174 CA $202 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Haymarket-Hotels-Hilton-Garden-Inn-Haymarket.h73560131.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) ![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 (1007) "Love this hotel and the location. Staff is super friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Casey CA $178 CA $201 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.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) ![Indoor pool](https://images.trvl-media.com/lodging/5000000/4540000/4532700/4532660/ec2efbf3.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) ![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) ### Hampton Inn & Suites Charles Town Charles Town 9.4/10 Exceptional (1011) "Great stay for a quick day trip to visit family. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $156 CA $175 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Martinsburg-Hotels-Hampton-Inn-Suites-Charles-Town.h4532660.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) ![Free buffet breakfast](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/fcd6e875.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Charles Town by IHG Charles Town 9.2/10 Wonderful (1007) "Great stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gwinn CA $139 CA $157 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Martinsburg-Hotels-Holiday-Inn-Express-Charles-Town.h1554858.Hotel-Information) ![Snack bar](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/bf8dce02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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 Winchester 9.0/10 Wonderful (756) "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 3 - Dec 4 [](https://www.expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.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) ![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) ![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) ![Lobby](https://images.trvl-media.com/lodging/3000000/2940000/2933800/2933741/5aa6585c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Extended Stay America Select Suites Gainesville Gainesville 6.2/10 (477) "Amazing place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Evelyn CA $99 CA $114 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Gainesville-Hotels-WoodSpring-Suites-Gainesville-VA.h2933741.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/d78ffc9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/ffce1877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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 Winchester 9.2/10 Wonderful (2236) "A run of the mill motel good for a travel break." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CARL CA $131 CA $143 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.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) ![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) ![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) ### The Inn at Charles Town - Hollywood Casino Charles Town 8.6/10 Excellent (514) "Staff was courteous….helpful…room was clean and comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $351 CA $407 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1830000/1828900/1828858/a5edbe69.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) ![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) ### Hampton Inn by Hilton Gainesville-Haymarket Gainesville 8.8/10 Excellent (979) "This is our second stay here .Everyone here at this location is always so courteous and pleasant." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea CA $118 CA $134 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Gainesville-Hotels-Hampton-Inn-By-Hilton-Gainesville-Haymarket.h1828858.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) ![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) ![Seasonal outdoor pool, open 9:00 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1370000/1360400/1360309/0a61ab6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Goodstone Inn & Restaurant Middleburg 9.6/10 Exceptional (48) "It was a delightful quaint exclusive country inn - a real treat to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda CA $532 CA $731 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Middleburg-Hotels-Goodstone-Inn-Restaurant.h1360309.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 Winchester 9.0/10 Wonderful (506) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DONNA D CA $134 CA $152 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Winchester-Hotels-Hilton-Garden-Inn-Winchester.h2169428.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10100/10086/80605b25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Warrenton Warrenton 6.4/10 (1002) "We had a one-night stay. Our room was clean and comfortable and the staff was friendly and welcoming. Would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carolyn CA $95 CA $102 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/Warrenton-Hotels-Baymont-By-Wyndham-Warrenton.h10086.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19220000/19217900/19217874/cbf060ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/20000000/19220000/19217900/19217874/d112b913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/20000000/19220000/19217900/19217874/8a8239cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/20000000/19220000/19217900/19217874/8de1d566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Charles Town Charles Town 9.6/10 Exceptional (797) "They had the friendliest staff at any hotel we have stayed at" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $181 CA $203 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Martinsburg-Hotels-Home2-Suites-By-Hilton-Charles-Town.h19217874.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24600/24519/50060c31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets, alarm clocks](https://images.trvl-media.com/lodging/1000000/30000/24600/24519/85cd782c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/24600/24519/d587f3ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/24600/24519/9a0c6dc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Warrenton Warrenton 9.0/10 Wonderful (138) "Clean room, attentive staff, great breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle CA $153 CA $167 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Warrenton-Hotels-Hampton-Inn-Warrenton.h24519.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 (1003) "The room was very clean and the staff were friendly and courteous." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $106 CA $119 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/c7da6581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/9e90770a.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 Winchester 9.2/10 Wonderful (1006) "Staff are amazing stayed twice in a week and every one was so kind friendly and happy to have us The women who is in the breakfast room was super The rooms where clean and comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Koren CA $106 CA $116 total includes taxes & fees Dec 7 - Dec 8 [](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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/db46282e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/83ee60b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Winchester South-Stephens City by IHG Stephens City 8.2/10 Very good (798) "Nice stay and friendly people " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ALFRED CA $112 CA $122 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.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) ![Garden](https://images.trvl-media.com/lodging/33000000/32440000/32431200/32431174/c883192a.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) ### The Red Fox Inn & Tavern Downtown 9.6/10 Exceptional (400) "Everything was wonderful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Henry CA $410 CA $467 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Middleburg-Hotels-The-Red-Fox-Inn-Tavern.h32431174.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-11&endDate=2025-12-12®ionId=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 [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FUpperville-Hotels.d184116.Travel-Guide-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpperville-Hotels.d184116.Travel-Guide-Hotels) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=HTG_BF_PROMO_184116) ## 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=2025-12-11&endDate=2025-12-12&adults=2®ionId=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 ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Travelodge by Wyndham Winchester 160 Front Royal Pike Winchester VA CA $95 CA $104 total Dec 1 - Dec 2 includes taxes & fees 8.4/10 Very Good! (1,096 reviews) [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Baymont by Wyndham Warrenton](https://images.trvl-media.com/lodging/1000000/20000/10100/10086/ad87d83f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Baymont by Wyndham Warrenton 7379 Comfort Inn Drive Warrenton VA CA $95 CA $102 total Nov 29 - Nov 30 includes taxes & fees 6.2/10 (1,002 reviews) [](https://expedia.ca/Warrenton-Hotels-Baymont-By-Wyndham-Warrenton.h10086.Hotel-Information) ![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Comfort Inn & Suites Winchester 195 Kernstown Commons Blvd Winchester VA CA $130 CA $142 total Dec 2 - Dec 3 includes taxes & fees 9.4/10 Exceptional! (1,059 reviews) [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Microtel Inn & Suites by Wyndham Winchester 150 Faraday Plaza Winchester VA CA $104 CA $114 total Dec 14 - Dec 15 includes taxes & fees 9/10 Wonderful! (1,367 reviews) [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.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 $112 CA $129 total Dec 1 - Dec 2 includes taxes & fees 8.4/10 Very Good! (1,011 reviews) [](https://expedia.ca/Leesburg-Hotels-Red-Roof-Inn-Leesburg.h17577.Hotel-Information) ![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 Dec 18 - Dec 19 includes taxes & fees 9/10 Wonderful! (1,002 reviews) [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ## Hotels in Upperville with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg) 5 Star Hotels 2 properties [](https://expedia.ca/5Star-Upperville-Hotels.s50-0-d184116.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.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/20000000/19690000/19681400/19681371/84fffc75_z.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/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 109 properties [](https://expedia.ca/2Star-Upperville-Hotels.s20-0-d184116.Travel-Guide-Filter-Hotels) ## Recent reviews of Upperville hotels ![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg) ### Hampton Inn Winchester-University/Mall Area 5/5 Excellent "Checking in and out was a breeze Room was nice and clean" A verified traveller stayed at Hampton Inn Winchester-University/Mall Area Posted 22 hours ago [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 5/5 Excellent "Great stay!" A verified traveller stayed at Country Inn & Suites by Radisson, Winchester, VA Posted 1 day ago [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg) ### Microtel Inn & Suites by Wyndham Winchester 5/5 Excellent "Nice place, still quite new. " A verified traveller stayed at Microtel Inn & Suites by Wyndham Winchester Posted 2 days ago [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Red Roof Inn Leesburg, VA](https://images.trvl-media.com/lodging/1000000/20000/17600/17577/610f0a4e_y.jpg) ### Red Roof Inn Leesburg, VA 5/5 Excellent "Excellent room and courtous staff" A verified traveller stayed at Red Roof Inn Leesburg, VA Posted 3 days ago [](https://expedia.ca/Leesburg-Hotels-Red-Roof-Inn-Leesburg.h17577.Hotel-Information) ![Hilton Garden Inn Dulles North](https://images.trvl-media.com/lodging/3000000/2340000/2335200/2335184/b8108f6b_y.jpg) ### Hilton Garden Inn Dulles North 5/5 Excellent "The room was clean and spacious, and the options for breakfast were plentiful. Eggs, potatoes, bacon, and sausage were available in the warmers while the more traditional continental breakfast items were also available. Staff was very friendly and helpful. The pool was a great place to hang out between games The hotel met my family's needs." A verified traveller stayed at Hilton Garden Inn Dulles North Posted 3 days ago [](https://expedia.ca/Ashburn-Hotels-Hilton-Garden-Inn-Dulles-North.h2335184.Hotel-Information) ![Hampton Inn & Suites Charles Town](https://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 very friendly " A verified traveller stayed at Hampton Inn & Suites Charles Town Posted 4 days ago [](https://expedia.ca/Martinsburg-Hotels-Hampton-Inn-Suites-Charles-Town.h4532660.Hotel-Information) ![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg) ### Comfort Inn & Suites Winchester 5/5 Excellent "Front desk was great! Room very nice" A verified traveller stayed at Comfort Inn & Suites Winchester Posted 4 days ago [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![Holiday Inn Express Charles Town by IHG](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/89e72fbd_y.jpg) ### Holiday Inn Express Charles Town by IHG 5/5 Excellent "Everyone we came in contact with were very nice and friendly. The buffet was really great. There was something for everyone. The coffee was very good. We will definitely be back when we next visit the casino. Very nice room. " A verified traveller stayed at Holiday Inn Express Charles Town by IHG Posted 4 days ago [](https://expedia.ca/Martinsburg-Hotels-Holiday-Inn-Express-Charles-Town.h1554858.Hotel-Information) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg) ### Travelodge by Wyndham Winchester 5/5 Excellent "Clean and comfortable." A verified traveller stayed at Travelodge by Wyndham Winchester Posted 5 days ago [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ## Frequently asked questions ### When is the best time to go to Upperville? > The most popular time to visit Upperville is in May, when the countryside bursts into bloom and the weather is pleasantly warm. With average temperatures hovering around 20°C, it's an excellent period for enjoying the scenic landscapes and participating in outdoor activities such as hiking, horseback riding, and visiting local wineries. > > > > During the peak season, which spans from April to June, Upperville attracts numerous visitors eager to experience its charming atmosphere and vibrant events. This thriving time of year is superb for those who appreciate quality experiences, as you can immerse yourself in the local culture with various festivals and community gatherings. The delightful climate complements outdoor adventures, allowing you to explore the picturesque trails and enjoy the breathtaking views that this region has to offer. > > > > If you're seeking a more tranquil experience, consider visiting in October. This month tends to be less crowded, offering a peaceful ambience while still allowing you to appreciate the stunning fall foliage and partake in seasonal activities like apple picking and vineyard tours. ### 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 Upperville. ### How can I save on a Upperville hotel booking with Expedia? > With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Upperville hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings. ### How much is the nightly rate at a Upperville hotel? > Prices for hotels in Upperville often vary, but you can find a great deal from CA $102 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. 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