Title: Book the Best Hotels with POOL in Winchester in 2026 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/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__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Winchester Hotels with a Pool Tonight [Mar 24 - Mar 25](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-03-24&endDate=2026-03-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 25 - Mar 26](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-03-25&endDate=2026-03-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-03-27&endDate=2026-03-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-04-03&endDate=2026-04-05&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) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/b20fa3f2.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) ![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.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) Winchester 9.0/10 Wonderful (829 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 CA $127 CA $138 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.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) ![Exterior](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb.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) ![Fitness facility](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/d8a75afe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Winchester [](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) Winchester 9.2/10 Wonderful (2,279 reviews) "Great hotel stay for our trip down soutg! Very clean and very nice rooms- very quiet!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy CA $147 CA $160 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.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) ![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) ![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.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) Front Royal 9.0/10 Wonderful (1,004 reviews) "Clean, staff was very polite and efficient." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marc CA $119 CA $131 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/w3840h2556x0y4-810f7f7f.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/w3840h2556x0y4-a519cf5a.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.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) Front Royal 9.0/10 Wonderful (1,004 reviews) "Great breakfast and nice room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly CA $140 CA $155 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.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) ![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/71000000/70930000/70921100/70921061/5447905f.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) ### Microtel Inn & Suites by Wyndham Winchester [](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) Winchester 9.2/10 Wonderful (1,452 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 CA $120 CA $130 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.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.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) Winchester 8.8/10 Excellent (1,000 reviews) "Very clean rooms and friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine CA $125 CA $136 total includes taxes & fees Apr 13 - Apr 14 [](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.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.ca/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) Stephens City 8.2/10 Very good (839 reviews) "Yes. Parking was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $121 CA $131 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.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/2000000/1370000/1364100/1364026/50dde1f0.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.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) Old Town Winchester 9.4/10 Exceptional (1,000 reviews) "Location of hotel is great for walking to restaurants and shops. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $168 CA $190 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/ee4df7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (Additional Living Area)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/aeec97ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Holiday Inn Winchester Se-Historic Gateway by IHG [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) Winchester 9.0/10 Wonderful (1,005 reviews) "very nice hotel,very clean" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Maria CA $107 CA $121 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.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) ![Down comforters, 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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/1b2ad59b.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) ### Courtyard by Marriott Winchester [](https://www.expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) Winchester 9.0/10 Wonderful (948 reviews) "Staff is friendly and the rooms are clean. Location is convenient to everything in Winchester " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $147 CA $160 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-04-07&endDate=2026-04-08®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 4 stars 5 stars Spa ## Hotels with pools and free breakfast in Winchester ![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) ![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) ### SpringHill Suites by Marriott Winchester [](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) Winchester 9.4/10 Exceptional (826) CA $156 CA $170 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/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) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/ffce1877.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) ![Fitness facility](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/d8a75afe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Winchester [](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) Winchester 9.2/10 Wonderful (2279) CA $147 CA $160 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/08af73b4.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) ![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.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) Winchester 9.0/10 Wonderful (829) CA $127 CA $138 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/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) ![Studio, 1 King Bed, Non Smoking, Refrigerator & Microwave (Wet bar)](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) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/0ec10473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester N/Conference Center, VA [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) Winchester 9.2/10 Wonderful (870) CA $145 CA $164 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.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](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/71000000/70930000/70921100/70921061/7284efb7.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.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) Winchester 9.2/10 Wonderful (1452) CA $120 CA $130 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/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) ![Suite, 1 King Bed (Additional Living Area)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/aeec97ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/7ff8d7be.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.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) Winchester 9.0/10 Wonderful (1005) CA $107 CA $121 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/4500/4419/4a54bb78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/4500/4419/28c2a2c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4500/4419/472dffdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/4500/4419/726eef71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Stephens City - Winchester South [](https://www.expedia.ca/Winchester-Hotels-Quality-Inn-Stephens-City-Winchester-South.h4419.Hotel-Information) Stephens City 8.0/10 Very good (644) CA $113 CA $123 total includes taxes & fees Apr 7 - Apr 8 [](https://www.expedia.ca/Winchester-Hotels-Quality-Inn-Stephens-City-Winchester-South.h4419.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) ![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) ![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.ca/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) Stephens City 8.2/10 Very good (839) CA $121 CA $131 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/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.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) Winchester 8.8/10 Excellent (1000) CA $125 CA $136 total includes taxes & fees Apr 13 - Apr 14 [](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Snack bar](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/bf8dce02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/25562c26.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) ### TRU By Hilton Winchester [](https://www.expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information) Winchester 9.0/10 Wonderful (803) CA $134 CA $146 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2026-04-07&endDate=2026-04-08®ionId=6056879&adults=2&amenities=POOL&sort=RECOMMENDED&mealPlan=FREE_BREAKFAST&openPlayBack=true) ## Top Winchester Hotel Reviews ![Hampton Inn Martinsburg](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/c1c4db32_y.jpg) ### Hampton Inn Martinsburg 8/10 Good "The front desk worker was very kind to me and my family :)" [](https://expedia.ca/Martinsburg-Hotels-Hampton-Inn-Martinsburg.h63064.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 6/10 Okay "Convenient location. The pool is clean and fitness facility is quite good. Breakfast is excellent and in good service." [](https://expedia.ca/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 "Room was clean, lobby and staff friendly. This is our second time staying so we always enjoy coming." [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.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 "I think this is the cutest place to stay that makes you feel warm and cozy! I like the views from the Terrance on the third floor too. I would stay here every time I came to this area. " [](https://expedia.ca/Luray-Hotels-Mimslyn-Inn-Historic-Hotels-Of-America.h9760491.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 "Perfect" [](https://expedia.ca/Leesburg-Hotels-Lansdowne-Resort-And-Spa.h27700.Hotel-Information) ![Fairfield Inn & Suites by Marriott Winchester](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/0de00556_y.jpg) ### Fairfield Inn & Suites by Marriott Winchester 10/10 Excellent "Right off 81 with several restaurants nearby. Spacious rooms" [](https://expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) ![Hilton Garden Inn Dulles North](https://images.trvl-media.com/lodging/3000000/2340000/2335200/2335184/d7802d8b_y.jpg) ### Hilton Garden Inn Dulles North 8/10 Good "Room had some lamp bulb issues… the front desk didn’t get that info to maintenance but I ran into a maintenance man and he took care of it right away. Thank you! " [](https://expedia.ca/Ashburn-Hotels-Hilton-Garden-Inn-Dulles-North.h2335184.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 8/10 Good "The room was very clean. The staff are friendly. Nice place to stay. " [](https://expedia.ca/Winchester-Hotels-Sleep-Inn-Suites.h892882.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 "Staff is friendly and the rooms are clean. Location is convenient to everything in Winchester " [](https://expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Winchester with outdoor pools? > [Hampton Inn Winchester N/Conference Center, VA](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) also shines in the outdoor pool category, providing a refreshing space for relaxation after a day of exploration. With a matching review score of 9.2, this hotel impresses visitors with its friendly and helpful staff, as well as its comfortable rooms. The complimentary breakfast buffet is another highlight that families appreciate, adding to the convenience of their stay. > > > For those who prefer a hotel near shopping and university areas, [Hampton Inn Winchester-University/Mall Area](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) is a solid option featuring an outdoor pool. With a traveller rating of 9.0, guests praise the staff for being friendly and amazing, while praising the clean rooms and great breakfast offerings. The location makes it superb for families looking to explore local attractions. > > > [Courtyard by Marriott Winchester](https://www.expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information), though primarily offering an indoor pool, also caters to families looking for a comfortable stay with a review score of 8.8\. Its amenities, including spacious suites and convenient self-parking, make it a practical choice for travellers. > > > Lastly, [TownePlace Suites by Marriott Winchester](https://www.expedia.ca/Winchester-Hotels-TownePlace-Suites-By-Marriott-Winchester.h2745505.Hotel-Information) features an outdoor pool and is known for its attentive staff and spotless rooms, also scoring an 8.8\. Families will appreciate the free continental breakfast and the good coffee available, ensuring a pleasant start to their day. ### How much does a hotel with outdoor pool in Winchester cost? ### Is it cheaper to book flights and a hotel in Winchester as a package? ### How can I save on a hotel in Winchester with Expedia? ### Can I cancel my hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - More ways to book - [3 Star Hotels in Old Town Winchester ](https://www.expedia.ca/3Star-Old-Town-Winchester-Winchester-Hotels.s30-n6164092-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Stephens City ](https://www.expedia.ca/4Star-Stephens-City-Hotels.s40-0-d12076.Travel-Guide-Filter-Hotels) - [Hotels near Apple Blossom Mall ](https://www.expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) - [Historic Hotels in Berryville ](https://www.expedia.ca/Berryville-Hotels-Historic-Hotel.0-0-d184082-tHistoricHotel.Travel-Guide-Filter-Hotels) - 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[Appleland Sports Center ](https://www.expedia.ca/Appleland-Sports-Center-Stephens-City.d553248621587477489.Vacation-Attraction) - [Jim Barnett Park ](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) - [Visit Millwood ](https://www.expedia.ca/Millwood.dx3000460156) - [Book Hotels with a Pool in Winchester on Expedia.com ](https://www.expedia.com/Winchester-Hotels-Hotel-With-Pool.0-0-d6056879-tHotelwithPool.Travel-Guide-Filter-Hotels)