Title: Book the Best Hotels with POOL in Winchester in 2026 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d7876.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d7876.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d7876.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d7876.Destination-Travel-Guides) ![Thanks to my friend of mine who's recommended me to this spot easy hike short walk to get there ](https://images.trvl-media.com/place/7876/9403688e-dbbb-4255-9528-8bddb2ed4db3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Nawa Aseen ![](https://images.trvl-media.com/place/7876/9403688e-dbbb-4255-9528-8bddb2ed4db3.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 [Jan 31 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-01-31&endDate=2026-02-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 1 - Feb 2](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-02-01&endDate=2026-02-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-02-06&endDate=2026-02-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-02-13&endDate=2026-02-15&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/25000000/24370000/24362600/24362582/04a3c81a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Accessible Bathtub (Accessible Tub)](https://images.trvl-media.com/lodging/25000000/24370000/24362600/24362582/60809f32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/25000000/24370000/24362600/24362582/3474fa42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/25000000/24370000/24362600/24362582/fa38a8d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Lexington East - Winchester by IHG [](https://www.expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Lexington-East-Winchester.h24362582.Hotel-Information) Winchester 9.4/10 Exceptional (538 reviews) "Clean room and friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tyson CA $125 CA $138 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Lexington-East-Winchester.h24362582.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/690f0ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/w5755h3835x5y5-d8ce41cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/c153c2fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds, Non Smoking, Kitchenette](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/w5755h3840x5y0-9326c0b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Winchester Hotel [](https://www.expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information) Winchester 8.4/10 Very good (1,000 reviews) "Clean room, friendly and fast check in service and had a great nights sleep " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $97 CA $107 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/w3840h2558x0y0-bdc9b429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Accessible, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/83fc2e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/93f7fc7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/51af70a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.Hotel-Information) Winchester 9.2/10 Wonderful (456 reviews) "Would stay there again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia CA $159 CA $176 total includes taxes & fees Feb 7 - Feb 8 [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/430000/422700/422677/023d86ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/422700/422677/c7af9b8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/430000/422700/422677/1f4d5f1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/430000/422700/422677/f6477704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Winchester [](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Winchester.h422677.Hotel-Information) Winchester 7.2/10 Good (775 reviews) "Great place for a reasonable price! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Whitney CA $103 CA $113 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Winchester.h422677.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/df000477.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/acf9d056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/1ed60932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/f0e4d2f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Winchester [](https://www.expedia.ca/Lexington-Hotels-Comfort-Inn.h327866.Hotel-Information) Winchester 7.0/10 Good (354 reviews) "This was the second time we’ve stopped here this year. It’s the perfect halfway respite between our home town and our destination. Very clean and comfortable. We will tag this as a regular stop on other trips. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Noelle CA $97 CA $107 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Lexington-Hotels-Comfort-Inn.h327866.Hotel-Information) ![Indoor pool, open 5:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/130000/123900/123895/b7d6b7de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/123900/123895/8d79aa69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, memory foam beds, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/130000/123900/123895/43c15bef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/130000/123900/123895/51e2f643.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Lexington Horse Park Area by IHG [](https://www.expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Lexington-Horse-Park-Area-By-IHG.h123895.Hotel-Information) Lexington 9.4/10 Exceptional (2,226 reviews) "Room was clean, staff was very helpful, easy parking, decent breakfast" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Christian CA $108 CA $125 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Lexington-Horse-Park-Area-By-IHG.h123895.Hotel-Information) ![Indoor spa tub](https://images.trvl-media.com/lodging/1000000/540000/532100/532007/0a069022.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/540000/532100/532007/db3edf18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking, Jetted Tub](https://images.trvl-media.com/lodging/1000000/540000/532100/532007/511a8efe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/540000/532100/532007/2dacd96b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Georgetown, KY [](https://www.expedia.ca/Lexington-Hotels-Country-Inn-Suites-By-Radisson.h532007.Hotel-Information) Georgetown 9.0/10 Wonderful (1,001 reviews) "Great stay! The hotel is clean, quite, and friendly. The breakfast bar was really good, too. Will definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah CA $105 CA $116 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Lexington-Hotels-Country-Inn-Suites-By-Radisson.h532007.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/ebd7e3b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 2 Bedrooms, Kitchen | Living area](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/324d2660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 2 Bedrooms, Kitchen | In-room dining](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/c7bf72a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 2 Bedrooms, Kitchen | Terrace/patio](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/278782c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Natural Bridge State Resort Park [](https://www.expedia.ca/Slade-Hotels-Natural-Bridge-State-Resort-Park.h15437778.Hotel-Information) Slade 8.6/10 Excellent (1,797 reviews) "Friendly staff, convenient the have a restaurant and tavern on site. There is great hiking right out the back door. Appreciated a quiet stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly [](https://www.expedia.ca/Slade-Hotels-Natural-Bridge-State-Resort-Park.h15437778.Hotel-Information) ![Seasonal outdoor pool, open 9 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/810000/800900/800890/95ce5c3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/810000/800900/800890/ecb98882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/810000/800900/800890/77f13e33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/800900/800890/a83dfff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Richmond [](https://www.expedia.ca/Lexington-Hotels-Quality-Inn.h800890.Hotel-Information) Richmond 9.0/10 Wonderful (1,001 reviews) "The room was clean and the bed was super comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $127 CA $140 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Lexington-Hotels-Quality-Inn.h800890.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/8b1776b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Accessible, Non Smoking (Mobility/Hearing Impaired Accessible)](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/a4d4a758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/8b90557f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/a7a31dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Lexington South / Hamburg [](https://www.expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.Hotel-Information) Lexington 8.8/10 Excellent (1,203 reviews) "Yes a very nice hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dale CA $118 CA $137 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.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=2026-02-14&endDate=2026-02-15®ionId=7876&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![Hyatt Regency Lexington](https://images.trvl-media.com/lodging/1000000/10000/3500/3461/c0c49295_y.jpg) ### Hyatt Regency Lexington 10/10 Excellent "Overall, it's good. The room is clean. The breakfast is delicious, but you have to order it yourself, which is relatively expensive." [](https://expedia.ca/Lexington-Hotels-Hyatt-Regency-Lexington.h3461.Hotel-Information) ![Spark by Hilton Lexington Hamburg](https://images.trvl-media.com/lodging/1000000/10000/6700/6639/4dbc3493_y.jpg) ### Spark by Hilton Lexington Hamburg 10/10 Excellent "Everything was great. Thank you." [](https://expedia.ca/Lexington-Hotels-Spark-By-Hilton-Lexington-Hamburg.h6639.Hotel-Information) ![The Campbell House Lexington, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/30000/27100/27029/2fd2c43b_y.jpg) ### The Campbell House Lexington, Curio Collection by Hilton 10/10 Excellent "Love staying here when visiting Lexington! This particular stay, we were upgraded to the presidential suite. What a fabulous surprise! We love the Campbell House. Great location if you have a student at UK or just in town for a horse race. " [](https://expedia.ca/Lexington-Hotels-The-Campbell-House-Lexington.h27029.Hotel-Information) ![Embassy Suites by Hilton Lexington Green](https://images.trvl-media.com/lodging/1000000/10000/1600/1598/1dd182aa_y.jpg) ### Embassy Suites by Hilton Lexington Green 10/10 Excellent "Very clean, and the made to order complimentary breakfast was excellent. " [](https://expedia.ca/Lexington-Hotels-Embassy-Suites-By-Hilton-Lexington-Green.h1598.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Lexington South / Hamburg](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/8b90557f_y.jpg) ### La Quinta Inn & Suites by Wyndham Lexington South / Hamburg 10/10 Excellent "Yes a very nice hotel " [](https://expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.Hotel-Information) ![Country Inn & Suites by Radisson, Georgetown, KY](https://images.trvl-media.com/lodging/1000000/540000/532100/532007/2dacd96b_y.jpg) ### Country Inn & Suites by Radisson, Georgetown, KY 10/10 Excellent "Yes. Everything was great" [](https://expedia.ca/Lexington-Hotels-Country-Inn-Suites-By-Radisson.h532007.Hotel-Information) ![Fairfield Inn & Suites by Marriott Lexington North](https://images.trvl-media.com/lodging/3000000/2810000/2803700/2803646/6ec64b2f_y.jpg) ### Fairfield Inn & Suites by Marriott Lexington North 10/10 Excellent "Check in was quick and easy. Friendly staff. The room was clean and comfortable, perfect for our one night stay and quick visit. " [](https://expedia.ca/Lexington-Hotels-Fairfield-Inn-Suites-By-Marriott-Lexington-North.h2803646.Hotel-Information) ![DoubleTree Suites by Hilton Hotel Lexington](https://images.trvl-media.com/lodging/1000000/10000/9900/9900/f18d8c34_y.jpg) ### DoubleTree Suites by Hilton Hotel Lexington 10/10 Excellent "Clean room love this place" [](https://expedia.ca/Lexington-Hotels-DoubleTree-Suites-By-Hilton-Hotel-Lexington.h9900.Hotel-Information) ![Hilton Lexington/Downtown](https://images.trvl-media.com/lodging/1000000/10000/2200/2101/b9ab6063_y.jpg) ### Hilton Lexington/Downtown 10/10 Excellent "Nice quiet room. Staff were very helpful." [](https://expedia.ca/Lexington-Hotels-Hilton-LexingtonDowntown.h2101.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Winchester with outdoor pools? > Another solid option is the [Best Western Winchester Hotel](https://www.expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information), featuring an outdoor pool that enhances its family-friendly appeal. Rated 8.4 by travellers, this hotel is praised for its spacious and clean rooms, friendly staff, and a great breakfast selection. With free self-parking and wired internet available, guests appreciate the thoughtful amenities that add to their overall experience. > > > For those on a budget, the [Baymont by Wyndham Winchester](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Winchester.h422677.Hotel-Information) presents a more economical choice. Although it has a lower review score of 7.2, it still offers an outdoor pool along with free Wi-Fi and breakfast options. Guests have noted the excellent size of the rooms and the wonderful staff, making it a decent value for families looking for a fun getaway. ### How much does a hotel with outdoor pool in Winchester cost? ### Are there hotels with outdoor pools that are close to Lykins Park? > Another great option is the [Best Western Winchester Hotel](https://www.expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information), boasting a solid review rating of 8.4\. This hotel features an inviting outdoor pool along with clean and sizable rooms. Families will particularly enjoy the hearty breakfast offerings and the friendly service provided by the staff, making it a welcoming spot for both relaxation and adventure. > > > If you're looking for a more budget-friendly choice, consider the [Baymont by Wyndham Winchester](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Winchester.h422677.Hotel-Information). With a traveller rating of 7.2, this hotel offers an outdoor pool and convenient amenities like free WiFi and continental breakfast. Guests have noted the excellent room sizes and the wonderful service from the staff, making it a practical option for families wanting to enjoy their time near Lykins Park without breaking the bank. ### 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 - Cars - Vacation Rental - Other - More ways to book - [Hotels near Applebee s Park ](https://www.expedia.ca/Applebee-S-Park-Hotels.0-l553248621557921127-0.Travel-Guide-Filter-Hotels) - [Motels in Camargo ](https://www.expedia.ca/Camargo-Motels.d553248634998850038-aaMotels.Travel-Guide-Accommodation) - [Chevy Chase Hotels ](https://www.expedia.ca/Chevy-Chase-Lexington-Hotels.0-n553248635976481361-0.Travel-Guide-Filter-Hotels) - [Hotels near Claiborne Farm ](https://www.expedia.ca/Claiborne-Farm-Hotels.0-l553248621559866398-0.Travel-Guide-Filter-Hotels) - 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