Title: Hotels in Upperville, VA - Best Upperville Hotels from £49 - Fully Refundable Options - Expedia.co.uk [Holiday Rentals in Upperville](https://expedia.co.uk/Upperville-Holiday-Rentals.d184116.Travel-Guide-HolidayRentals)[Upperville Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Upperville.d184116.Car-Hire-Guide)[Upperville Holidays](https://expedia.co.uk/Upperville.d184116.Holidays-City-Breaks) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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.co.uk/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-01-31&d1=2026-01-31&endDate=2026-02-02&d2=2026-02-02&amenities=SPA_ON_SITE) Pool [](https://www.expedia.co.uk/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-01-31&d1=2026-01-31&endDate=2026-02-02&d2=2026-02-02&amenities=POOL) Cabin [](https://www.expedia.co.uk/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-01-31&d1=2026-01-31&endDate=2026-02-02&d2=2026-02-02&lodging=CABIN) Apart­ment [](https://www.expedia.co.uk/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-01-31&d1=2026-01-31&endDate=2026-02-02&d2=2026-02-02&lodging=APARTMENT) Family friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-01-31&d1=2026-01-31&endDate=2026-02-02&d2=2026-02-02&travelerType=family_friendly) Pet friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-01-31&d1=2026-01-31&endDate=2026-02-02&d2=2026-02-02&amenities=PETS) Hot tub [](https://www.expedia.co.uk/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-01-31&d1=2026-01-31&endDate=2026-02-02&d2=2026-02-02&amenities=HOT_TUB) Cottage [](https://www.expedia.co.uk/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-01-31&d1=2026-01-31&endDate=2026-02-02&d2=2026-02-02&lodging=COTTAGE) Waterpark [](https://www.expedia.co.uk/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-01-31&d1=2026-01-31&endDate=2026-02-02&d2=2026-02-02&amenities=WATER_PARK) Farm [](https://www.expedia.co.uk/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2026-01-31&d1=2026-01-31&endDate=2026-02-02&d2=2026-02-02&lodging=AGRITOURISM) ## Check prices for these dates Tonight [17 Jan - 18 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=184116&startDate=2026-01-17&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [18 Jan - 19 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=184116&startDate=2026-01-18&endDate=2026-01-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [23 Jan - 25 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=184116&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [30 Jan - 1 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=184116&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Upperville hotels ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/9e66afda.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) ![Fitness facility](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/d8a75afe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Winchester [](https://www.expedia.co.uk/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) Winchester 9.2/10 Wonderful (2,246 reviews) "yes, room was spotless very nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ROBERT £75 includes taxes & fees 19 Jan - 20 Jan [](https://www.expedia.co.uk/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.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) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/c5cff2bc.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 [](https://www.expedia.co.uk/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) Winchester 9.2/10 Wonderful (1,003 reviews) "Great stay, as usual" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary £67 includes taxes & fees 6 Feb - 7 Feb [](https://www.expedia.co.uk/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking | Desk, blackout curtains, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/557f4fea.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) ![Free daily self-service breakfast ](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/c6c8c1e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Winchester [](https://www.expedia.co.uk/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) Winchester 9.4/10 Exceptional (1,096 reviews) "We have stayed here many times on our way to Massachusetts and find it perfect every time." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patsy £80 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/a391dd61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/b42e7086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/f49e1754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/39b30783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Winchester, VA [](https://www.expedia.co.uk/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) Winchester 8.8/10 Excellent (1,001 reviews) "Clean efficient room with good front desk service. Convienence to Highway 81 and eateries." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris £66 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/10b5cc1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/d565eb6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Double Beds, Non Smoking | In-room safe, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/325feec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast ](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/4749606b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Front Royal Near Shenandoah National Park [](https://www.expedia.co.uk/Front-Royal-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information) Front Royal 7.6/10 Good (1,001 reviews) "Good condition " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Phillip £52 includes taxes & fees 19 Jan - 20 Jan [](https://www.expedia.co.uk/Front-Royal-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/c93a366a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/636f5ae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillow-top beds, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/67555e67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/8a97ffc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Winchester [](https://www.expedia.co.uk/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) Winchester 9.4/10 Exceptional (798 reviews) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rene £82 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Free on-the-go breakfast ](https://images.trvl-media.com/lodging/2000000/1110000/1101900/1101849/60a92697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1110000/1101900/1101849/0367093c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1110000/1101900/1101849/5a11bccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cots/infant beds](https://images.trvl-media.com/lodging/2000000/1110000/1101900/1101849/c25e3790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Warrenton by IHG [](https://www.expedia.co.uk/Warrenton-Hotels-Holiday-Inn-Express-Hotel-Suites-Warrenton.h1101849.Hotel-Information) Warrenton 8.6/10 Excellent (776 reviews) "Convenient location for my business trip spacious, and clean, thank you" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert £70 includes taxes & fees 22 Jan - 23 Jan [](https://www.expedia.co.uk/Warrenton-Hotels-Holiday-Inn-Express-Hotel-Suites-Warrenton.h1101849.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/ac575b89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/b2c1f0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom | Living area | 48-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/5df91a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/cd7ad69b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Winchester [](https://www.expedia.co.uk/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) Winchester 9.0/10 Wonderful (1,003 reviews) "Good hotel on our road trip" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janet £65 includes taxes & fees 8 Feb - 9 Feb [](https://www.expedia.co.uk/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/0de00556.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/b20fa3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Select Comfort beds, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/b107c420.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) ### Fairfield Inn & Suites by Marriott Winchester [](https://www.expedia.co.uk/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) Winchester 9.0/10 Wonderful (815 reviews) "We stay here a lot and it is always consistently clean and service is great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim £75 includes taxes & fees 20 Jan - 21 Jan [](https://www.expedia.co.uk/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/1b2ad59b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/8f242b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Down duvets, Select Comfort beds, desk, laptop workspace](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/fa968ddc.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) ### Courtyard by Marriott Winchester [](https://www.expedia.co.uk/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) Winchester 9.0/10 Wonderful (927 reviews) "Room was great. Staff was extremely friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy £82 includes taxes & fees 23 Jan - 24 Jan [](https://www.expedia.co.uk/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) ![Casino](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/90e3a6e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/ec380243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/b5631713.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) ### Clarion Inn Harpers Ferry - Charles Town [](https://www.expedia.co.uk/Martinsburg-Hotels-Clarion-Inn-Harpers-Ferry-Charles-Town.h977326.Hotel-Information) Harpers Ferry 7.8/10 Good (1,003 reviews) "Overall, this hotel was clean, quiet, a good option to explore Harper's Ferry. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessie £75 includes taxes & fees 25 Jan - 26 Jan [](https://www.expedia.co.uk/Martinsburg-Hotels-Clarion-Inn-Harpers-Ferry-Charles-Town.h977326.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking | Desk, laptop workspace, iron/ironing board, free cots/infant beds](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) ![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/7284efb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Microtel Inn & Suites by Wyndham Winchester [](https://www.expedia.co.uk/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) Winchester 9.2/10 Wonderful (1,433 reviews) "Clean room and bathroom, friendly staff, helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas £66 includes taxes & fees 26 Jan - 27 Jan [](https://www.expedia.co.uk/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Snack bar](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/e84bf2ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/0c5c6174.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 [](https://www.expedia.co.uk/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information) Winchester 9.0/10 Wonderful (788 reviews) "Clean room, good breakfast, easy check in/out." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph £63 includes taxes & fees 26 Jan - 27 Jan [](https://www.expedia.co.uk/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.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/d236d605.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (Additional Living Area) | In-room safe, desk, laptop workspace, blackout curtains](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 [](https://www.expedia.co.uk/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) Winchester 9.0/10 Wonderful (1,003 reviews) "Nice clean room, friendly staff, and the restaurant was very good." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan £66 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/2fa2dbbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed, Non Smoking, Refrigerator & Microwave (Wet bar) | Premium bedding, pillow-top beds, in-room safe, individually furnished](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/5daa33ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/1d5ecc9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/ca692cd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester N/Conference Center, VA [](https://www.expedia.co.uk/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) Winchester 9.2/10 Wonderful (855 reviews) "Super clean room comfy beds" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joy £90 includes taxes & fees 24 Jan - 25 Jan [](https://www.expedia.co.uk/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/19e0634f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Smoking | Living area | LED TV](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/bf0bfb1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Smoking | Living area | LED TV](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/38eadba9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Winchester [](https://www.expedia.co.uk/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) Winchester 8.6/10 Excellent (1,065 reviews) "Hotels well Located off 81 for a nice pull Off and overnight stay. Staff is friendly and helpful and rooms comfortable and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stefanie £57 includes taxes & fees 19 Jan - 20 Jan [](https://www.expedia.co.uk/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/83ee60b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually furnished, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/fde0973a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/ab6f1ae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Winchester South-Stephens City by IHG [](https://www.expedia.co.uk/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) Stephens City 8.2/10 Very good (813 reviews) "Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rose £60 includes taxes & fees 25 Jan - 26 Jan [](https://www.expedia.co.uk/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/d92b1c53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/4c7ae30b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/9cf3d079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows [](https://www.expedia.co.uk/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) Front Royal 9.0/10 Wonderful (1,001 reviews) "Great room and staff. Nice restaurant and bar also with good prices. Very nice hotel. 5 stars" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vincent £80 includes taxes & fees 25 Jan - 26 Jan [](https://www.expedia.co.uk/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5707228d.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/a8e7d0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/31f87045.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The George Washington Hotel, A Wyndham Grand Hotel [](https://www.expedia.co.uk/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) Old Town Winchester 9.4/10 Exceptional (1,007 reviews) "Great hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CHARLES £107 includes taxes & fees 25 Jan - 26 Jan [](https://www.expedia.co.uk/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/554af346.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/502f6bec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast ](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/c9f83fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Non Smoking | Hypo-allergenic bedding, down duvets, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/8f2087d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Winchester near University [](https://www.expedia.co.uk/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information) Winchester 7.8/10 Good (1,000 reviews) "great stay with breakfast too" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James £62 includes taxes & fees 26 Jan - 27 Jan [](https://www.expedia.co.uk/Winchester-Hotels-Sleep-Inn-Suites.h892882.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.co.uk/Hotel-Search?startDate=2026-02-01&endDate=2026-02-02®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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FUpperville-Hotels.d184116.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpperville-Hotels.d184116.Travel-Guide-Hotels) ## Stay near popular Upperville attractions ### Upperville Park Explore the great outdoors at Upperville Park, a lovely green space in Upperville. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909174232272232448) ## 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.co.uk/Hotel-Search?startDate=2026-02-01&endDate=2026-02-02&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 ## Top Upperville Hotel Reviews ![TownePlace Suites by Marriott Front Royal](https://images.trvl-media.com/lodging/37000000/36350000/36342700/36342604/0776aa15_y.jpg) ### TownePlace Suites by Marriott Front Royal 10/10 Excellent "Clean room, friendly and helpful staff, good breakfast, I would stay again." [](https://expedia.co.uk/Winchester-Hotels-TownePlace-Suites-By-Marriott-Front-Royal.h36342604.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "yes, room was spotless very nice place to stay" [](https://expedia.co.uk/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![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 10/10 Excellent "Pet friendly and they provided a goodie bag for my dog - very welcoming." [](https://expedia.co.uk/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![Best Western Leesburg Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/12700/12669/d621c756_y.jpg) ### Best Western Leesburg Hotel & Conference Center 10/10 Excellent "Breakfast was fresh, nice quiet pleasant place " [](https://expedia.co.uk/Leesburg-Hotels-Best-Western-Leesburg-Hotel-Conference-Center.h12669.Hotel-Information) ![Holiday Inn Express & Suites Leesburg - Historic District by IHG](https://images.trvl-media.com/lodging/1000000/600000/596500/596430/6cf9400d_y.jpg) ### Holiday Inn Express & Suites Leesburg - Historic District by IHG 10/10 Excellent "Excellent stay except on Saturday night someone had a dog whining from 2 am till around 3 am someplace below our room…. Was tough trying to sleep." [](https://expedia.co.uk/Leesburg-Hotels-Comfort-Suites-Leesburg.h596430.Hotel-Information) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "C'était propre et tranquille" [](https://expedia.co.uk/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.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 10/10 Excellent "Everything was great" [](https://expedia.co.uk/Ashburn-Hotels-Hilton-Garden-Inn-Dulles-North.h2335184.Hotel-Information) ![Lansdowne Resort and Spa](https://images.trvl-media.com/lodging/1000000/30000/27700/27700/5ae32850_y.jpg) ### Lansdowne Resort and Spa 10/10 Excellent "Loved the resort, the spa, everyone was so sweet. It was clean and smelled amazing. I had the absolute best massage ever. Love love love, me and my husband definitely will be back " [](https://expedia.co.uk/Leesburg-Hotels-Lansdowne-Resort-And-Spa.h27700.Hotel-Information) ![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg) ### Comfort Inn & Suites Winchester 10/10 Excellent "Great staff" [](https://expedia.co.uk/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ## More cheap stays in Upperville ![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 £49 1 Feb - 2 Feb includes taxes & fees 6.4/10 (1,000 reviews) [](https://expedia.co.uk/Warrenton-Hotels-Baymont-By-Wyndham-Warrenton.h10086.Hotel-Information) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Travelodge by Wyndham Winchester 160 Front Royal Pike Winchester VA £57 19 Jan - 20 Jan includes taxes & fees 8.4/10 Very Good! (1,064 reviews) [](https://expedia.co.uk/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 £65 1 Feb - 2 Feb includes taxes & fees 8.4/10 Very Good! (1,000 reviews) [](https://expedia.co.uk/Leesburg-Hotels-Red-Roof-Inn-Leesburg.h17577.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 £66 26 Jan - 27 Jan includes taxes & fees 9/10 Wonderful! (1,426 reviews) [](https://expedia.co.uk/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.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 £80 1 Feb - 2 Feb includes taxes & fees 9.4/10 Exceptional! (1,095 reviews) [](https://expedia.co.uk/Winchester-Hotels-Comfort-Inn-Suites.h57958244.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 £86 25 Jan - 26 Jan includes taxes & fees 9/10 Wonderful! (1,000 reviews) [](https://expedia.co.uk/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ## Frequently asked questions ### What is the best area to stay in Upperville? > Upperville's village centre is small and picturesque, primarily centred around the intersection of John S. Mosby Highway (Route 50) and Trappe Road. This area is characterised by its historic stone and brick buildings, many of which house boutique shops, art galleries, and acclaimed dining establishments. The iconic Trinity Episcopal Church is a prominent landmark, and the area is surrounded by rolling hills and horse farms, providing a scenic backdrop. > > > Couples looking for a romantic and sophisticated getaway will find the village centre particularly appealing. You'll be within easy walking distance of gourmet restaurants for intimate dinners and unique shops for browsing. The relaxed pace and beautiful surroundings make it ideal for a quiet escape. > > > For those interested in equestrian activities, staying in the village centre provides excellent access to the renowned Upperville Colt & Horse Show grounds, which are just a short drive away. ### When is the best time to go to Upperville? > Spring brings blooming dogwoods and redbuds, making it an ideal time for outdoor activities like horseback riding or visiting local vineyards. The Upperville Colt & Horse Show, a significant equestrian event, usually takes place in early June, drawing many visitors to the area. > > > Autumn offers stunning foliage as the trees along the Blue Ridge Mountains turn vibrant shades of red, orange, and gold. This season is great for scenic drives, exploring the historic villages nearby, and enjoying the numerous harvest festivals and farm-to-table dining experiences. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Upperville hotel booking with Expedia? ### How much is the nightly rate at a Upperville hotel? ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - More ways to book - [Airlie Hotels ](https://www.expedia.co.uk/Airlie-Hotels.d55540.Travel-Guide-Hotels) - [Aldie Hotels ](https://www.expedia.co.uk/Aldie-Hotels.d553248622877094266.Travel-Guide-Hotels) - [Hotels near Aspen Dale Winery at the Barn ](https://www.expedia.co.uk/Aspen-Dale-Winery-At-The-Barn-Hotels.0-l553248621532661858-0.Travel-Guide-Filter-Hotels) - [Berryville Hotels ](https://www.expedia.co.uk/Berryville-Hotels.d184082.Travel-Guide-Hotels) - [Cabin Rentals in Blue Ridge ](https://www.expedia.co.uk/Blue-Ridge-Cabins.d553248635976006713-aaCabins.Travel-Guide-Accommodation) - 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[Aspen Dale Winery at the Barn ](https://www.expedia.co.uk/Aspen-Dale-Winery-At-The-Barn-Delaplane.d553248621532661858.Attraction) - [Barns of Rose Hill ](https://www.expedia.co.uk/Barns-Of-Rose-Hill-Berryville.d553248621561864687.Attraction) - [Berryville Holidays ](https://www.expedia.co.uk/Berryville.d184082.Holidays-City-Breaks) - [Visit Bluemont ](https://www.expedia.co.uk/Bluemont.dx6348602) - [Boyce Holidays ](https://www.expedia.co.uk/Boyce.d184084.Holidays-City-Breaks) - [Cobbler Mountain Cellars ](https://www.expedia.co.uk/Cobbler-Mountain-Cellars-Delaplane.d553248621532661860.Attraction) - [Dinosaur Land ](https://www.expedia.co.uk/Dinosaur-Land-White-Post.d553248621532661835.Attraction) - [Visit Front Royal ](https://www.expedia.co.uk/Front-Royal.dx7312) - [Glenwood Park ](https://www.expedia.co.uk/Glenwood-Park-Middleburg.d553248621532661869.Attraction) - [Visit Linden ](https://www.expedia.co.uk/Linden.dx3000460101) - [Mackintosh Fruit Farm ](https://www.expedia.co.uk/Mackintosh-Fruit-Farm-Berryville.d553248621532661930.Attraction) - [National Sporting Library & Museum ](https://www.expedia.co.uk/National-Sporting-Library-Museum-Middleburg.d553248621532661872.Attraction) - [Visit Paeonian Springs ](https://www.expedia.co.uk/Paeonian-Springs.dx3000355237) - [Philip Carter Winery ](https://www.expedia.co.uk/Philip-Carter-Winery-Hume.d553248621532661855.Attraction) - [Visit Purcellville ](https://www.expedia.co.uk/Purcellville.dx6338641) - [Quattro Goomba's Winery ](https://www.expedia.co.uk/Quattro-Goombas-Winery-Aldie.d553248621532661904.Attraction) - [Visit Round Hill ](https://www.expedia.co.uk/Round-Hill.dx3000460647) - [Visit The Plains ](https://www.expedia.co.uk/The-Plains.dx3000460694) - [Ace New Zealand Rental Cars in Riverton ](https://www.expedia.co.uk/ACE-New-Zealand-Car-Rentals-In-Riverton.d553248635975849884-c1106.Car-Rental-Guide-Suppliers) - [Car hire Aldie ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Aldie.d553248622877094266.Car-Hire-Guide) - [Car hire Front Royal ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Front-Royal.d7312.Car-Hire-Guide) - 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[Things to do in Bluemont ](https://www.expedia.co.uk/Things-To-Do-In-Bluemont.d6348602.Travel-Guide-Activities) - [Book Hotels in Upperville on Expedia.com ](https://www.expedia.com/Upperville-Hotels.d184116.Travel-Guide-Hotels) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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