Title: Book the Best Hotels with POOL in Winchester Historic District in 2026 | Expedia.ca [Winchester Historic District Travel Guide](https://expedia.ca/Winchester-Winchester-Historic-District.dx918789051029594112)[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 Historic District Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester-Historic-District.d918789051029594112.Car-Rental-Guide)[Winchester Historic District Vacations](https://expedia.ca/Winchester-Historic-District.d918789051029594112.Destination-Travel-Guides) ![A nice 3 block outdoor downtown shopping area with dining and bars also. ](https://images.trvl-media.com/place/6056879/3acc501a-a330-4063-b538-b2368ef6a4c5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Fernando Begay # Find Hotels with a Pool in Winchester Historic District, VA from CA $109 - ![](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 Historic District Hotels with a Pool Tonight [Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-12-18&endDate=2025-12-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-12-19&endDate=2025-12-20&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester Historic District hotels with a pool ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/bff9ad76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/a8e7d0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5707228d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The George Washington Hotel, A Wyndham Grand Hotel [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) Old Town Winchester 9.4/10 Exceptional (1004) "Great hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CHARLES CA $174 CA $197 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/0c5c6174.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/c99442ce.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 (770) "Very nice room and common spaces. Breakfast was good and the price was very fair." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $100 CA $109 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.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) ![Property amenity](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/8897f4a2.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/71000000/70930000/70921100/70921061/5447905f.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 (1383) "Clean room great helpful staff good breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Loretta CA $102 CA $111 total includes taxes & fees Jan 4 - Jan 5, 2026 [](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) ![Reception](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/51a72e04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/5e25574f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/67cbe2e0.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) "Have stayed here multiple times -always good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $114 CA $124 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.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) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/b6f40366.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) ### 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 (1000) "Great room cozy bed fabulous restaurant great staff on property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joyce CA $96 CA $109 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.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) ![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/b1a55fc4.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 (2229) "Rooms are always clean when I stay and the staff was very friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley CA $123 CA $133 total includes taxes & fees Dec 25 - Dec 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/43000000/42550000/42543800/42543772/b4a66759.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/164a5d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/57a6dfe3.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.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) Winchester 9.4/10 Exceptional (783) "The staff were friendly and knowledgeable . Clean room and breakfast was excellent. Hotel close to restaurants and stores. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yolanda CA $139 CA $151 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/7d9ba7bf.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) ![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/2000000/1500000/1497900/1497898/723a3b2f.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 (915) "comfortable room, amenities and staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Prashant CA $139 CA $151 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/64922bcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/ad5604d4.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) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/b96d495c.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 (1000) "Friendly staff, nice clean room, hotel restaurant was delicious. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dorothy CA $134 CA $148 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/cd85ec17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/e8983c22.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 Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/9e90770a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Winchester [](https://www.expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) Winchester 9.2/10 Wonderful (1000) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaron CA $104 CA $113 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2026-01-01&endDate=2026-01-02®ionId=918789051029594112&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Historic District Hotel Reviews ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "Yes" [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "Couldnt be happier with my stay. Check in was easy, rooms were clean and bed bug free, there was a fridge, coffee maker and microwave! Easy shampoo, conditioner, body wash dispenser in the shower, the kids LOVED the heated indoor pool! There is coffee and hot chocolate in the lobby available At ALL TIMES. The continental breakfast was top notch! Even had sausage gravy! And! 711 was right next door incase you forget your phone charger (guilty)! And if you just wanted a little late night relax without going anywhere, they have a cooler upfront with some high noons and other wines for purchase. I will definitely recommend and definitely go back!" [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "Was nice and peaceful no issues " [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "The room was clean and the bed was comfortable. My only desire is for firmer, foam pillows and brighter lights at the vanity. The staff is always efficient and friendly. It’s a beautiful hotel and we always have a good time at the bar!" [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Hampton Inn Front Royal](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0_y.jpg) ### Hampton Inn Front Royal 10/10 Excellent "All great " [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.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 "Clean room, quiet area, good breakfast" [](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Quality Inn Winchester](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943_y.jpg) ### Quality Inn Winchester 10/10 Excellent "Everything was great, including breakfast " [](https://expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) ![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg) ### Hampton Inn Winchester-University/Mall Area 10/10 Excellent "Room was quiet and comfy and staff were friendly! Entry way was decorated for the holidays!" [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![Spark by Hilton Winchester](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/ac575b89_y.jpg) ### Spark by Hilton Winchester 10/10 Excellent "good" [](https://expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Winchester Historic District? ### What is there to see and do in Winchester Historic District? ### When is the best time to book a hotel with a pool in Winchester Historic District? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [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) - 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