Title: The Best Winchester Hotels with Pools - 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 30 - Mar 31](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-03-30&endDate=2026-03-31&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 31 - Apr 1](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-03-31&endDate=2026-04-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-04-03&endDate=2026-04-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-04-10&endDate=2026-04-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester 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 (830 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 Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/1d5ecc9d.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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/2fa2dbbe.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 (870 reviews) "The staff was wonderful! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jayne $106 nightly $120 total Apr 18 - Apr 19 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/2000000/1500000/1497900/1497898/c267eed3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/723a3b2f.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/1b2ad59b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Winchester [](https://www.expedia.com/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) Winchester 9.0/10 Wonderful (950 reviews) "Great location" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) jim $107 nightly $116 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) ![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/2000000/1890000/1889100/1889081/9874bc44.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.com/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) Front Royal 9.0/10 Wonderful (1,002 reviews) "Clean, staff was very polite and efficient." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marc $87 nightly $96 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.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) ![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) ### 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) "Room was clean, lobby and staff friendly. This is our second time staying so we always enjoy coming." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miriam $107 nightly $117 total Mar 31 - Apr 1 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/71000000/70930000/70921100/70921061/3e194222.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/5447905f.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) ### 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 (1,460 reviews) "Everything,room was amazing, staff so friendly, breakfast very good " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Douglas Gary $88 nightly $96 total Apr 19 - Apr 20 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.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) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/c93a366a.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/43000000/42550000/42543800/42543772/8a97ffc7.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 (826 reviews) "Beautiful hotel and room. Accessible room was perfect. Staff was friendly right from check-in. Would highly recommend this hotel to anyone who needs an accessible room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew $114 nightly $124 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.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) ![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/cb88e2d2.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 (841 reviews) "Yes. Parking was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John $97 nightly $106 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/a391dd61.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) ![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.com/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) Winchester 8.8/10 Excellent (1,001 reviews) "Very clean rooms and friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine $91 nightly $99 total Apr 20 - Apr 21 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/1000000/180000/172900/172810/c5cff2bc.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) ![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) ### Quality Inn Winchester [](https://www.expedia.com/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) Winchester 9.2/10 Wonderful (1,000 reviews) "Everything was perfect. Would highly recommend this hotel" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Phyllis $88 nightly $96 total Apr 6 - Apr 7 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=2026-04-13&endDate=2026-04-14®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 ![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) ![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) ### 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 (830) $93 nightly $101 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.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) ![Reception](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/9e2916b6.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) ![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) ### 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 (870) $106 nightly $120 total Apr 18 - Apr 19 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.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) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/8a97ffc7.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) ### SpringHill Suites by Marriott Winchester [](https://www.expedia.com/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) Winchester 9.4/10 Exceptional (826) $114 nightly $124 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.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) ![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 (2280) $107 nightly $117 total Mar 31 - Apr 1 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/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) ![Exterior](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/3eaf7092.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 (1460) $88 nightly $96 total Apr 19 - Apr 20 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.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 drapes](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.com/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) Winchester 9.0/10 Wonderful (1005) $91 nightly $99 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.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) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/6b04791b.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.com/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) Winchester 8.8/10 Excellent (1001) $91 nightly $99 total Apr 20 - Apr 21 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/2000000/1890000/1889100/1889081/204cbf3a.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) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/d92b1c53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows [](https://www.expedia.com/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) Front Royal 9.0/10 Wonderful (1002) $87 nightly $96 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/c7da6581.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) $88 nightly $96 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/37000000/36350000/36342700/36342604/50595509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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 (568) $124 nightly $137 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-TownePlace-Suites-By-Marriott-Front-Royal.h36342604.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=2026-04-13&endDate=2026-04-14®ionId=6056879&adults=2&amenities=POOL&sort=RECOMMENDED&mealPlan=FREE_BREAKFAST&openPlayBack=true) ## Top Winchester Hotel Reviews ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/19e0634f_y.jpg) ### Travelodge by Wyndham Winchester 4/10 Poor "There were croaches in my room and ants. Nedding had burn holes. And someone tried to get in my room in the middle of the night." [](https://expedia.com/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.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 "Easy parking, spacious clean rooms, staff friendly and courteous." [](https://expedia.com/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.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 "Great stay" [](https://expedia.com/Leesburg-Hotels-Lansdowne-Resort-And-Spa.h27700.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 4/10 Poor "The staff was extremely unpleasant to me." [](https://expedia.com/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.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 "We had a quick stop for a few hour rest. We " [](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 8/10 Good "Friendly staff." [](https://expedia.com/Martinsburg-Hotels-Hampton-Inn-Martinsburg.h63064.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 location. Classy old property " [](https://expedia.com/Winchester-Hotels-The-George-Washington-Hotel.h1364026.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 6/10 Okay "I only stayed for about an hour. The room was freezing cold as it was dead of winter and freezing out. There was no heat turned on in the room when I got there so it was quite a while before the room actually reached a tolerable temperature" [](https://expedia.com/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information) ![Mimslyn Inn Historic Hotels Of America](https://images.trvl-media.com/lodging/10000000/9770000/9760500/9760491/5175eb5d_y.jpg) ### Mimslyn Inn Historic Hotels Of America 10/10 Excellent "Luray is a relaxing place meant for enjoying the beauty of the Blue Ridge mountains, the Shenandoah Valley, and a slower pace. There is adventure in fishing, rafting, hiking, and biking. There are no Gallerias or Malls. It is lovely and refreshing. The Mimslyn is perfect. The breakfast in the Circa 31 room is exceptional. The dinner and a drink in the Speakeasy is well done and much appreciated after a day exploring the area. We spent time fishing the South Fork Shenandoah and then came “home” to our base at the Mimslyn. Core memories." [](https://expedia.com/Luray-Hotels-Mimslyn-Inn-Historic-Hotels-Of-America.h9760491.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) - [Hotels with Restaurants in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Restaurants.0-n6164092-0-tHotelswithRestaurants.Travel-Guide-Filter-Hotels) - [Casino Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Casino-Hotel.0-n6164092-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - 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[Flights from Houston (IAH) to Winchester (WGO) ](https://www.expedia.com/lp/flights/iah/wgo/houston-to-winchester) - [Flights from Washington (IAD) to Winchester (WGO) ](https://www.expedia.com/lp/flights/iad/wgo/washington-to-winchester) - [Flights from Baltimore (BWI) to Winchester (WGO) ](https://www.expedia.com/lp/flights/bwi/wgo/baltimore-to-winchester) - [Flights from Pittsburgh (PIT) to Winchester (WGO) ](https://www.expedia.com/lp/flights/pit/wgo/pittsburgh-to-winchester) - [Flights from Washington (DCA) to Winchester (WGO) ](https://www.expedia.com/lp/flights/dca/wgo/washington-to-winchester) - [Flights from Dallas (DFW) to Winchester (WGO) ](https://www.expedia.com/lp/flights/dfw/wgo/dallas-to-winchester) - [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) - 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[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) - 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