Title: The Best Upperville Hotels with Pools from $80 - Hotels with indoor pools in Upperville, VA | Expedia.com [Upperville Travel Guide](https://expedia.com/Upperville.dx184116)[Hotels in Upperville](https://expedia.com/Upperville-Hotels.d184116.Travel-Guide-Hotels)[Vacation Rentals in Upperville](https://expedia.com/Upperville-Vacation-Rentals.d184116.Travel-Guide-VacationRentals)[Flights to Upperville](https://expedia.com/Cheap-Flights-To-Upperville.d184116.Travel-Guide-Flights)[Car Rentals in Upperville](https://expedia.com/Car-Rentals-In-Upperville.d184116.Car-Rental-Guide)[Upperville Vacation Packages](https://expedia.com/Upperville.d184116.Destination-Travel-Guides) ![Welcome sign to Upperville Virginia in Fauquier County.](https://images.trvl-media.com/place/184116/deb8a32e-602b-43b9-802d-e775f9221444.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/184116/deb8a32e-602b-43b9-802d-e775f9221444.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Upperville Hotels with a Pool Tonight [Mar 10 - Mar 11](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-03-10&endDate=2026-03-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 11 - Mar 12](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-03-11&endDate=2026-03-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-03-13&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=184116&startDate=2026-03-20&endDate=2026-03-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Upperville hotels with a pool ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/f063e2e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/08af73b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Winchester [](https://www.expedia.com/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) Winchester 9.0/10 Wonderful (824 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 $93 nightly $101 total Mar 13 - Mar 14 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/bff9ad76.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/d6b37fa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### The George Washington Hotel, A Wyndham Grand Hotel [](https://www.expedia.com/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) Old Town Winchester 9.4/10 Exceptional (1,008 reviews) "Great hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CHARLES $122 nightly $138 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/810f7f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/54c3ac5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/40efde4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch LCD TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/6c4fd659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Front Royal [](https://www.expedia.com/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) Front Royal 9.0/10 Wonderful (1,003 reviews) "Room was spotless, place was quiet and our welcome at the desk was perfect" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Merrill $104 nightly $115 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![Seasonal outdoor pool, open 9 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/971b2ca9.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/cb88e2d2.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) ### Holiday Inn Express Winchester South-Stephens City by IHG [](https://www.expedia.com/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) Stephens City 8.2/10 Very Good (830 reviews) "The room was spotless, staff is excellent. Well, recommend the stay to everyone I know" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelso $87 nightly $95 total Mar 21 - Mar 22 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/a0b970f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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, pillowtop 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) ![Reception](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/9e2916b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester N/Conference Center, VA [](https://www.expedia.com/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) Winchester 9.2/10 Wonderful (867 reviews) "The staff was wonderful! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jayne $106 nightly $120 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/37000000/36350000/36342700/36342604/dff66771.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/37000000/36350000/36342700/36342604/50595509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36350000/36342700/36342604/673fcd79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/37000000/36350000/36342700/36342604/dcb5b936.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TownePlace Suites by Marriott Front Royal [](https://www.expedia.com/Winchester-Hotels-TownePlace-Suites-By-Marriott-Front-Royal.h36342604.Hotel-Information) Front Royal 9.6/10 Exceptional (565 reviews) "Clean room, friendly and helpful staff, good breakfast, I would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine $116 nightly $128 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-TownePlace-Suites-By-Marriott-Front-Royal.h36342604.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/5000000/4540000/4532700/4532660/ec2efbf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4540000/4532700/4532660/4441f7ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/5000000/4540000/4532700/4532660/973d5ee9.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 [](https://www.expedia.com/Martinsburg-Hotels-Hampton-Inn-Suites-Charles-Town.h4532660.Hotel-Information) Charles Town 9.4/10 Exceptional (1,005 reviews) "Great stay loved the pool area and breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chyrell $114 nightly $128 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Martinsburg-Hotels-Hampton-Inn-Suites-Charles-Town.h4532660.Hotel-Information) ![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 drapes, 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) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/6b04791b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/a391dd61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Winchester, VA [](https://www.expedia.com/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) Winchester 8.8/10 Excellent (1,002 reviews) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) gary $91 nightly $99 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/030e20be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, soundproofing, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/8303a152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/39d8617d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/7d6688ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Twi-Lite Inn [](https://www.expedia.com/Winchester-Hotels-Twi-Lite-Motel.h15799885.Hotel-Information) Front Royal 8.2/10 Very Good (547 reviews) "Clean, comfortable room. Staff was nice and I really enjoyed my stay. Motel was in a high traffic area, but still a quiet stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel $72 nightly $80 total Mar 11 - Mar 12 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Twi-Lite-Motel.h15799885.Hotel-Information) ![Seasonal outdoor pool, open 9:00 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1370000/1360400/1360309/e36e10c0.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1370000/1360400/1360309/4b804569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1370000/1360400/1360309/fc88c08e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Goodstone Inn & Restaurant [](https://www.expedia.com/Middleburg-Hotels-Goodstone-Inn-Restaurant.h1360309.Hotel-Information) Middleburg 9.6/10 Exceptional (50 reviews) "Unfortunately we did not get to spend lots of time on the property (other than sleeping and breakfast), but everything was great and we will definitely try to come back and spend more time at the Goodstone. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Conny $430 nightly $490 total Mar 11 - Mar 12 Total with taxes and fees [](https://www.expedia.com/Middleburg-Hotels-Goodstone-Inn-Restaurant.h1360309.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.com/Hotel-Search?startDate=2026-03-24&endDate=2026-03-25®ionId=184116&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Upperville Breakfast included 4 stars 5 stars Hot tub Spa ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AFFINITY_SPRING_PROMO_184116) ## Top Upperville Hotel Reviews ![Holiday Inn Express & Suites Leesburg - Historic District by IHG](https://images.trvl-media.com/lodging/1000000/600000/596500/596430/c6a38a54_y.jpg) ### Holiday Inn Express & Suites Leesburg - Historic District by IHG 10/10 Excellent "The room was clean and spacious. I was very happy with the quick and easy check-in/check-out process too. Would totally recommend. 5 stars!" [](https://expedia.com/Leesburg-Hotels-Holiday-Inn-Express-And-Suites-Leesburg-Historic-District.h596430.Hotel-Information) ![Holiday Inn Express Hotel & Suites Warrenton by IHG](https://images.trvl-media.com/lodging/2000000/1110000/1101900/1101849/60a92697_y.jpg) ### Holiday Inn Express Hotel & Suites Warrenton by IHG 10/10 Excellent "Keep it up" [](https://expedia.com/Warrenton-Hotels-Holiday-Inn-Express-Hotel-Suites-Warrenton.h1101849.Hotel-Information) ![Sleep Inn & Suites Winchester near University](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/554af346_y.jpg) ### Sleep Inn & Suites Winchester near University 2/10 Terrible "Killed a " [](https://expedia.com/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information) ![Holiday Inn Express Charles Town by IHG](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/d75699e6_y.jpg) ### Holiday Inn Express Charles Town by IHG 10/10 Excellent "The shuttle to anywhere in a 2 mile radius was a real bonus! Best yet, the shuttle was "on demand" and we walked right on it once and had a very short wait for the return trip. The breakfast buffet was plentiful for a good start to the morning! We enjoyed our short stay and likely will be back!" [](https://expedia.com/Martinsburg-Hotels-Holiday-Inn-Express-Charles-Town.h1554858.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/9e66afda_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "The hotel was conveniently located in town, even for a guest without a car on hand! Staff was AMAZING! Breakfast was solid and on time! Clean rooms and easy to navigate. " [](https://expedia.com/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Home2 Suites by Hilton Charles Town](https://images.trvl-media.com/lodging/20000000/19220000/19217900/19217874/cbf060ec_y.jpg) ### Home2 Suites by Hilton Charles Town 10/10 Excellent "No complaints. The staff was amazing. Room was nice. The breakfast was good. " [](https://expedia.com/Martinsburg-Hotels-Home2-Suites-By-Hilton-Charles-Town.h19217874.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 "I have stayed at Landsdowne many years, typically for girls spa weekends or overnight stay while I’m in town. The Spa Experience is always phenomenal. The staff is friendly all around. I continue to enjoy my stays!" [](https://expedia.com/Leesburg-Hotels-Lansdowne-Resort-And-Spa.h27700.Hotel-Information) ![Hampton Inn by Hilton Gainesville-Haymarket](https://images.trvl-media.com/lodging/2000000/1830000/1828900/1828858/718360d7_y.jpg) ### Hampton Inn by Hilton Gainesville-Haymarket 10/10 Excellent "Nice pool" [](https://expedia.com/Gainesville-Hotels-Hampton-Inn-By-Hilton-Gainesville-Haymarket.h1828858.Hotel-Information) ![Holiday Inn Winchester Se-Historic Gateway by IHG](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg) ### Holiday Inn Winchester Se-Historic Gateway by IHG 10/10 Excellent "very nice hotel,very clean" [](https://expedia.com/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Upperville? ### What is there to see and do in Upperville? ### When is the best time to book a hotel with a pool in Upperville? ## Explore a world of travel with Expedia - 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