Title: The Best Winchester Hotels with Pools from $72 - Hotels with indoor pools in Winchester, VA | Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx6056879)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.com/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d6056879.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.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 Winchester Hotels with a Pool Tonight [Mar 15 - Mar 16](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-03-15&endDate=2026-03-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 16 - Mar 17](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-03-16&endDate=2026-03-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-03-20&endDate=2026-03-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-03-27&endDate=2026-03-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester hotels with a pool ![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/cb88e2d2.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) ![Individually furnished, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/fde0973a.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 (835 reviews) - Splash into seasonal fun at this rural retreat with a refreshing pool and loungers. $87 nightly $95 total Mar 27 - Mar 28 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 (869 reviews) - Splash into summer with panoramic mountain views from this seasonal outdoor pool experience. $106 nightly $120 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/ffce1877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/41cd029b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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.com/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) Winchester 9.2/10 Wonderful (2,280 reviews) - Dive into the inviting indoor pool, perfect for year-round swims at this clean, modern hotel. $113 nightly $123 total Mar 18 - Mar 19 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/f063e2e9.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) ![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) ### 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 (825 reviews) - Splash into Winchester luxury with an indoor pool retreat in a historical Art Deco hotel. $93 nightly $101 total Mar 22 - Mar 23 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/2000000/1660000/1652900/1652833/b42e7086.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) ![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) - Splash into a year-round swimming oasis with a refreshing indoor pool sanctuary at this Winchester hotel. $91 nightly $99 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/636f5ae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/67555e67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/e6dc1dff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/c93a366a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Winchester [](https://www.expedia.com/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) Winchester 9.4/10 Exceptional (820 reviews) - Refresh in the indoor pool at this hotel that offers a firepit and streamlined amenities near top Winchester attractions. $105 nightly $114 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.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/2000000/1370000/1364100/1364026/5707228d.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) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/50dde1f0.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 (1,007 reviews) - Float in style at this historic Winchester hotel featuring an elegant indoor pool and indulgent spa services. $120 nightly $136 total Mar 30 - Mar 31 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/71000000/70930000/70921100/70921061/3e194222.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657.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) ![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/5447905f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Microtel Inn & Suites by Wyndham Winchester [](https://www.expedia.com/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) Winchester 9.2/10 Wonderful (1,440 reviews) - Make a splash at this Winchester hotel with an indoor pool and fitness center for all seasons. $85 nightly $92 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.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) ![Dining](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/7d6688ff.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) ![Desk, soundproofing, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/2186fef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Twi-Lite Inn [](https://www.expedia.com/Winchester-Hotels-Twi-Lite-Motel.h15799885.Hotel-Information) Front Royal 8.2/10 Very Good (547 reviews) - Discover a restful retreat with a pristine seasonal outdoor pool near Shenandoah National Park at this immaculately clean motel. $65 nightly $72 total Mar 16 - Mar 17 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Twi-Lite-Motel.h15799885.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 2 Double Beds, Non Smoking | Blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/cab65b9d.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.com/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) Winchester 9.2/10 Wonderful (1,000 reviews) - Dive into crystal-clear waters at this well-maintained hotel featuring a seasonal outdoor pool surrounded by pleasant landscaping. $84 nightly $92 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Quality-Inn.h172810.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=2026-03-29&endDate=2026-03-30®ionId=6056879&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Winchester Breakfast included Hot tub Spa 4 stars 5 stars ## Hotels with pools and free breakfast in Winchester ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/810f7f7f.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) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/40efde4b.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) ### Hampton Inn Front Royal [](https://www.expedia.com/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) Front Royal 9.0/10 Wonderful (1001) $104 nightly $115 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![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) ![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/41cd029b.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) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/ffce1877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Winchester [](https://www.expedia.com/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) Winchester 9.2/10 Wonderful (2280) $113 nightly $123 total Mar 18 - Mar 19 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.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) ![Select Comfort beds, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/b107c420.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 (825) $93 nightly $101 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.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 drapes](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.com/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) Stephens City 8.2/10 Very Good (835) $87 nightly $95 total Mar 27 - Mar 28 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/39b30783.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) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/b42e7086.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 (1002) $91 nightly $99 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.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) ![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) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/50dde1f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/d6b37fa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The George Washington Hotel, A Wyndham Grand Hotel [](https://www.expedia.com/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) Old Town Winchester 9.4/10 Exceptional (1007) $120 nightly $136 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-The-George-Washington-Hotel.h1364026.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) ![Pillowtop beds, desk, laptop workspace, blackout drapes](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.com/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) Winchester 9.4/10 Exceptional (820) $105 nightly $114 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Standard Double Room, 2 Double Beds, Non Smoking | Blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/cab65b9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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.com/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) Winchester 9.2/10 Wonderful (1000) $84 nightly $92 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Quality-Inn.h172810.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) ![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/5447905f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/3eaf7092.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.com/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) Winchester 9.2/10 Wonderful (1440) $85 nightly $92 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/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) ![Exterior](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/25562c26.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) ![Indoor pool](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/0c5c6174.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TRU By Hilton Winchester [](https://www.expedia.com/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information) Winchester 9.0/10 Wonderful (801) $89 nightly $97 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.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=2026-03-29&endDate=2026-03-30®ionId=6056879&adults=2&amenities=POOL&sort=RECOMMENDED&mealPlan=FREE_BREAKFAST&openPlayBack=true) ## Top Winchester Hotel Reviews ![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 "Didn’t use either. Breakfast was great" [](https://expedia.com/Martinsburg-Hotels-Holiday-Inn-Express-Charles-Town.h1554858.Hotel-Information) ![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/c10d527c_y.jpg) ### Hampton Inn Winchester-University/Mall Area 10/10 Excellent "Nice lobby, nice room, ample parking, good breakfast selection, good area around the hotel" [](https://expedia.com/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.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 "I don’t like to be negative, but I would not recommend this sleep inn. The first thing I noticed is the dirty carpets, smelly room, damaged door to the room, the room was run down , two exit doors were not secured, anybody can just walk in the building." [](https://expedia.com/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5707228d_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "Great stay!" [](https://expedia.com/Winchester-Hotels-The-George-Washington-Hotel.h1364026.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 "Not your average hotel. Unique room layout, modern lobby and friendly staff! " [](https://expedia.com/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Hampton Inn Martinsburg](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/c1c4db32_y.jpg) ### Hampton Inn Martinsburg 10/10 Excellent "Staff was extremely friendly and helpful! Loved the welcoming message from the front desk. Would definitely stay again!" [](https://expedia.com/Martinsburg-Hotels-Hampton-Inn-Martinsburg.h63064.Hotel-Information) ![Courtyard by Marriott Winchester](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/1b2ad59b_y.jpg) ### Courtyard by Marriott Winchester 10/10 Excellent "Great location" [](https://expedia.com/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.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 clean, nice bar/restaurant, convenient location. Excellent breakfast! Will definitely stay again when traveling 😄" [](https://expedia.com/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Best Western Leesburg Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/12700/12669/bcd21d29_y.jpg) ### Best Western Leesburg Hotel & Conference Center 10/10 Excellent "The staff is excellent" [](https://expedia.com/Leesburg-Hotels-Best-Western-Leesburg-Hotel-Conference-Center.h12669.Hotel-Information) ## Frequently asked questions ### What's it like visiting Winchester? ### What are some hotels with pools in Winchester? ### How many hotels with pools will I find in Winchester? ### What is there to see and do in Winchester? ### When is the best time to book a hotel with a pool in Winchester? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Historic Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Historic-Hotel.0-n6164092-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - 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[Flights from Charlotte (CLT) to Winchester (WGO) ](https://www.expedia.com/lp/flights/clt/wgo/charlotte-to-winchester) - [Flights from New York (JFK) to Winchester (WGO) ](https://www.expedia.com/lp/flights/jfk/wgo/new-york-to-winchester) - [Flights from Norfolk (ORF) to Winchester (WGO) ](https://www.expedia.com/lp/flights/orf/wgo/norfolk-to-winchester) - [Flights from Raleigh (RDU) to Winchester (WGO) ](https://www.expedia.com/lp/flights/rdu/wgo/raleigh-to-winchester) - [Flights from Knoxville (TYS) to Winchester (WGO) ](https://www.expedia.com/lp/flights/tys/wgo/knoxville-to-winchester) - [Flights from Chattanooga (CHA) to Winchester (WGO) ](https://www.expedia.com/lp/flights/cha/wgo/chattanooga-to-winchester) - [Flights from Atlanta (ATL) to Winchester (WGO) ](https://www.expedia.com/lp/flights/atl/wgo/atlanta-to-winchester) - [Flights from Philadelphia (PHL) to Winchester (WGO) ](https://www.expedia.com/lp/flights/phl/wgo/philadelphia-to-winchester) - [Flights from Chicago (ORD) to Winchester (WGO) ](https://www.expedia.com/lp/flights/ord/wgo/chicago-to-winchester) - [Flights from Seattle (SEA) to Winchester (WGO) ](https://www.expedia.com/lp/flights/sea/wgo/seattle-to-winchester) - [Flights from Boston (BOS) to Winchester (WGO) ](https://www.expedia.com/lp/flights/bos/wgo/boston-to-winchester) - [Flights from Nashville (BNA) to Winchester (WGO) ](https://www.expedia.com/lp/flights/bna/wgo/nashville-to-winchester) - [Flights from Orlando (MCO) to Winchester (WGO) ](https://www.expedia.com/lp/flights/mco/wgo/orlando-to-winchester) - [Flights from Greensboro (GSO) to Winchester (WGO) ](https://www.expedia.com/lp/flights/gso/wgo/greensboro-to-winchester) - [Flights from Columbus (CMH) to Winchester (WGO) ](https://www.expedia.com/lp/flights/cmh/wgo/columbus-to-winchester) - [Flights from Indianapolis (IND) to Winchester (WGO) ](https://www.expedia.com/lp/flights/ind/wgo/indianapolis-to-winchester) - [Flights from St. Louis (STL) to Winchester (WGO) ](https://www.expedia.com/lp/flights/stl/wgo/st-louis-to-winchester) - [Flights from Los Angeles (LAX) to Winchester (WGO) ](https://www.expedia.com/lp/flights/lax/wgo/los-angeles-to-winchester) - [Flights from Savannah (SAV) to Winchester (WGO) ](https://www.expedia.com/lp/flights/sav/wgo/savannah-to-winchester) - [Flights from San Diego (SAN) to Winchester (WGO) ](https://www.expedia.com/lp/flights/san/wgo/san-diego-to-winchester) - [Flights from Myrtle Beach (MYR) to Winchester (WGO) ](https://www.expedia.com/lp/flights/myr/wgo/myrtle-beach-to-winchester) - [Flights from Detroit (DTW) to Winchester (WGO) ](https://www.expedia.com/lp/flights/dtw/wgo/detroit-to-winchester) - [Flights from Jacksonville (JAX) to Winchester (WGO) ](https://www.expedia.com/lp/flights/jax/wgo/jacksonville-to-winchester) - [Flights from Tampa (TPA) to Winchester (WGO) ](https://www.expedia.com/lp/flights/tpa/wgo/tampa-to-winchester) - [Flights from Kansas City (MCI) to Winchester (WGO) ](https://www.expedia.com/lp/flights/mci/wgo/kansas-city-to-winchester) - [Flights to Winchester Regional ](https://www.expedia.com/Cheap-Flights-To-Winchester-Regional.d6033090.Travel-Guide-Flights) - [Flights from Minneapolis (MSP) to Winchester (WGO) ](https://www.expedia.com/lp/flights/msp/wgo/minneapolis-to-winchester) - [Flights from Cincinnati (CVG) to Winchester (WGO) ](https://www.expedia.com/lp/flights/cvg/wgo/cincinnati-to-winchester) - [Flights from Greenville (GSP) to Winchester (WGO) ](https://www.expedia.com/lp/flights/gsp/wgo/greenville-to-winchester) - [Flights from Grand Rapids (GRR) to Winchester (WGO) ](https://www.expedia.com/lp/flights/grr/wgo/grand-rapids-to-winchester) - [Visit Old Town Winchester ](https://www.expedia.com/Winchester-Old-Town-Winchester.dx6164092) - [Bright Box Theater ](https://www.expedia.com/Bright-Box-Theater-Old-Town-Winchester.d553248621561864843.Vacation-Attraction) - [Shenandoah Valley Discovery Museum ](https://www.expedia.com/Shenandoah-Valley-Discovery-Museum-Old-Town-Winchester.d553248621587527659.Vacation-Attraction) - [George Washington's Office ](https://www.expedia.com/George-Washingtons-Office-Old-Town-Winchester.d6164042.Vacation-Attraction) - [Mt Hebron Cemetery ](https://www.expedia.com/Mt-Hebron-Cemetery-Winchester.d553248621532661845.Vacation-Attraction) - [Patsy Cline Historic House ](https://www.expedia.com/Patsy-Cline-Historic-House-Winchester.d553248621532661841.Vacation-Attraction) - [Museum of the Shenandoah Valley ](https://www.expedia.com/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.Vacation-Attraction) - [Jim Barnett Park ](https://www.expedia.com/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) - [Abram's Delight ](https://www.expedia.com/Abrams-Delight-Winchester.d553248621532661839.Vacation-Attraction) - [Nalls Farm Market ](https://www.expedia.com/Nalls-Farm-Market-Winchester.d553248621532661846.Vacation-Attraction) - [Shenandoah University ](https://www.expedia.com/Shenandoah-University-Winchester.d6127311.Vacation-Attraction) - [Rock Harbor Golf Course ](https://www.expedia.com/Rock-Harbor-Golf-Course-Winchester.d553248621561864838.Vacation-Attraction) - [Car rentals near Old Town Winchester ](https://www.expedia.com/Car-Rentals-In-Old-Town-Winchester.d6164092.Car-Rental-Guide) - [Car rentals near Patsy Cline Historic House ](https://www.expedia.com/Car-Rentals-In-Patsy-Cline-Historic-House.d553248621532661841.Car-Rental-Guide) - [Car rentals near Nalls Farm Market ](https://www.expedia.com/Car-Rentals-In-Nalls-Farm-Market.d553248621532661846.Car-Rental-Guide) - [Car rentals near Shenandoah University ](https://www.expedia.com/Car-Rentals-In-Shenandoah-University.d6127311.Car-Rental-Guide) - [Van Car Rentals near Shenandoah University ](https://www.expedia.com/Van-Car-Rentals-In-Shenandoah-University.d6127311-tVan.Car-Rental-Guide-Class) - [Car rentals near Apple Blossom Mall ](https://www.expedia.com/Car-Rentals-In-Apple-Blossom-Mall.d6164018.Car-Rental-Guide) - [Car rentals near ValleyHealth Winchester Medical Center ](https://www.expedia.com/Car-Rentals-In-Winchester-Medical-Center.d6164057.Car-Rental-Guide) - [Car rentals near College Park ](https://www.expedia.com/Car-Rentals-In-College-Park.d553248635975870482.Car-Rental-Guide) - [Car rental Winchester Airport (WGO) ](https://www.expedia.com/Car-Rentals-In-Winchester-Regional.d6033090.Car-Rental-Guide)