Title: Book the Best Hotels with POOL in Winchester in 2025 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d553248634983495009.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d553248634983495009.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d553248634983495009.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d553248634983495009.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Winchester, MO from CA $143 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=553248634983495009&startDate=2025-10-01&endDate=2025-10-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=553248634983495009&startDate=2025-10-02&endDate=2025-10-03&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248634983495009&startDate=2025-10-03&endDate=2025-10-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248634983495009&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Hotels with a Pool ![Indoor pool, outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/50000/42200/42122/aadfb5be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/42200/42122/cb7cc1f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/50000/42200/42122/446bd1a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/50000/42200/42122/bfca870c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham Fenton 8.2/10 Very good (1045) "The staff was nice, breakfast was good, the location was convenient. " CA $124 CA $143 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/St-Louis-Hotels-Drury-Inn-Suites-St-Louis-Fenton.h42122.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1770000/1768200/1768149/9234fc04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/2000000/1770000/1768200/1768149/800a6847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/2000000/1770000/1768200/1768149/035dee6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1770000/1768200/1768149/9fbd251c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wildwood Hotel Wildwood 9.2/10 Wonderful (1578) "We enjoyed our stay!" CA $123 CA $148 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/St-Louis-Hotels-The-Wildwood-Hotel.h1768149.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/50000/40200/40112/8e60b31d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40200/40112/ef39d78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40200/40112/da3a948f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/50000/40200/40112/d7498121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pear Tree Inn St. Louis Arnold Arnold 9.2/10 Wonderful (1019) "Clean, comfortable and pleasant stay." CA $125 CA $145 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/St-Louis-Hotels-Pear-Tree-Inn-St-Louis-Arnold.h40112.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/50000/41500/41474/3d25ebf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/41500/41474/b6740445.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/41500/41474/d0798b8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/50000/41500/41474/e68647ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drury Inn & Suites St. Louis Airport Edmundson 9.2/10 Wonderful (1078) "Very clean, quite, good breakfast " CA $149 CA $175 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/St-Louis-Hotels-Drury-Inn-Suites-St-Louis-Airport.h41474.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/550000/546300/546271/812bbb9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/550000/546300/546271/532a2ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/550000/546300/546271/3c6c1cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/550000/546300/546271/78b2a688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drury Plaza Hotel St. Louis at the Arch Downtown St. Louis 9.4/10 Exceptional (3123) "Great staff and food " CA $189 CA $221 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/St-Louis-Hotels-Drury-Plaza-Hotel-St-Louis-At-The-Arch.h546271.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/670000/664500/664414/3b576caf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/670000/664500/664414/c082745a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/670000/664500/664414/b0afb49a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/670000/664500/664414/b493e570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites St Charles - St Louis St. Charles 8.4/10 Very good (1009) "Clean, mostly quiet, friendly staff. " CA $140 CA $161 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/St-Louis-Hotels-Comfort-Suites-St-Charles-St-Louis.h664414.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/40000/37700/37651/151222b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/37700/37651/fde81462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/40000/37700/37651/1dea3ddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/37700/37651/a847bb13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drury Inn & Suites St. Louis Union Station Downtown West 9.4/10 Exceptional (1267) " Love staying here!" CA $166 CA $197 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/St-Louis-Hotels-Drury-Inn-St-Louis-At-Union-Station.h37651.Hotel-Information) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/2000000/1720000/1717400/1717380/b693e67c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1720000/1717400/1717380/6d4358f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1720000/1717400/1717380/f3f5bbd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1720000/1717400/1717380/eb823de0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drury Inn & Suites St. Louis Forest Park Clifton Heights 9.4/10 Exceptional (1000) "Always a great stay " CA $160 CA $187 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/St-Louis-Hotels-Drury-Inn-Suites-St-Louis-Forest-Park.h1717380.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/15590000/15583900/15583887/9fba35aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/16000000/15590000/15583900/15583887/08db7b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/16000000/15590000/15583900/15583887/133d5cf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/16000000/15590000/15583900/15583887/28e7b062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites O'Fallon MO - Technology Drive O'Fallon 8.8/10 Excellent (1001) "I would stay here again." CA $124 CA $146 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/St-Louis-Hotels-Sleep-Inn-Suites-OFallon-MO-Technology-Drive.h15583887.Hotel-Information) ![Indoor pool, open 9:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/480000/471500/471447/1f68fced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/480000/471500/471447/365f1124.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/480000/471500/471447/c6adcbcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/480000/471500/471447/w2880h2092x0y14-c9fd3208.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites St. Louis/Chesterfield Chesterfield 8.8/10 Excellent (820) "Very safe area with lots of restaurants and shops nearby" CA $141 CA $164 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/St-Louis-Hotels-Hampton-Inn-Suites-St-LouisChesterfield.h471447.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=2025-10-15&endDate=2025-10-16®ionId=553248634983495009&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![Moonrise Hotel](//images.trvl-media.com/lodging/3000000/2300000/2292900/2292856/fe8445aa_y.jpg) ### Moonrise Hotel 10/10 Excellent "Clean room! Friendly and welcoming staff. " [](https://expedia.ca/St-Louis-Hotels-Moonrise-Hotel.h2292856.Hotel-Information) ![Drury Inn & Suites St. Louis Union Station](//images.trvl-media.com/lodging/1000000/40000/37700/37651/151222b4_y.jpg) ### Drury Inn & Suites St. Louis Union Station 10/10 Excellent "Staff was happy and helpful. Breakfast and evening snack were great! Tons of food. Room was clean and quiet. Hotel was clean and had great design and interior!" [](https://expedia.ca/St-Louis-Hotels-Drury-Inn-St-Louis-At-Union-Station.h37651.Hotel-Information) ![Marriott St. Louis Grand](//images.trvl-media.com/lodging/1000000/910000/904800/904712/4c313173_y.jpg) ### Marriott St. Louis Grand 10/10 Excellent "Clean" [](https://expedia.ca/St-Louis-Hotels-Marriott-St-Louis-Grand.h904712.Hotel-Information) ![Hyatt Regency St. Louis at The Arch](//images.trvl-media.com/lodging/1000000/20000/14900/14877/335a172e_y.jpg) ### Hyatt Regency St. Louis at The Arch 10/10 Excellent "Stunning views and excellent staff " [](https://expedia.ca/St-Louis-Hotels-Hyatt-Regency-St-Louis-At-The-Arch.h14877.Hotel-Information) ![DoubleTree by Hilton St. Louis Forest Park](//images.trvl-media.com/lodging/2000000/1090000/1082400/1082373/3f93ad2e_y.jpg) ### DoubleTree by Hilton St. Louis Forest Park 10/10 Excellent "No breakfast provided. Bathroom tub and toilet turn of the century. technology current even excellent. Ice machines didn't work. Parking places which cost $15.00. SIze of small compact car so a mess." [](https://expedia.ca/St-Louis-Hotels-DoubleTree-By-Hilton-St-Louis-Forest-Park.h1082373.Hotel-Information) ![Drury Plaza Hotel St. Louis at the Arch](//images.trvl-media.com/lodging/1000000/550000/546300/546271/78b2a688_y.jpg) ### Drury Plaza Hotel St. Louis at the Arch 10/10 Excellent "great location for our trip goals" [](https://expedia.ca/St-Louis-Hotels-Drury-Plaza-Hotel-St-Louis-At-The-Arch.h546271.Hotel-Information) ![Forest Park Hotel by MDR](//images.trvl-media.com/lodging/1000000/30000/22300/22298/21d70af8_y.jpg) ### Forest Park Hotel by MDR 10/10 Excellent "Love it " [](https://expedia.ca/St-Louis-Hotels-Holiday-Inn-St-Louis-Forest-Park.h22298.Hotel-Information) ![Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham](//images.trvl-media.com/lodging/1000000/50000/42200/42122/bfca870c_y.jpg) ### Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham 10/10 Excellent "Was very happy with our stay. Our suite was well worth the very reasonable price. King Bed was very comfortable. AC was a little noisy but no issues." [](https://expedia.ca/St-Louis-Hotels-Drury-Inn-Suites-St-Louis-Fenton.h42122.Hotel-Information) ![Pear Tree Inn St. Louis Near Union Station](//images.trvl-media.com/lodging/1000000/30000/26600/26572/0bb9dbf3_y.jpg) ### Pear Tree Inn St. Louis Near Union Station 10/10 Excellent "clean, well maintained, friendly courteous staff, excellent breakfast" [](https://expedia.ca/St-Louis-Hotels-Pear-Tree-Inn-St-Louis-Near-Union-Station.h26572.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Winchester? > [Drury Plaza Hotel St. Louis at the Arch](https://www.expedia.ca/St-Louis-Hotels-Drury-Plaza-Hotel-St-Louis-At-The-Arch.h546271.Hotel-Information): Hotel, 5-minute walk from Gateway Arch. Features buffet, an indoor pool, and complimentary wireless internet access. [Clayton Plaza Hotel & Extended Stay](https://www.expedia.ca/St-Louis-Hotels-Clayton-Plaza-Hotel-Extended-Stay.h18144.Hotel-Information): Hotel located near Washington University in St. Louis. Offers a sauna, an indoor pool, and full. [Hyatt Regency St. Louis at The Arch](https://www.expedia.ca/St-Louis-Hotels-Hyatt-Regency-St-Louis-At-The-Arch.h14877.Hotel-Information): Features buffet, a seasonal outdoor pool, and free self parking. [Pear Tree Inn St. Louis Airport](https://www.expedia.ca/St-Louis-Hotels-Pear-Tree-Inn-St-Louis-Airport.h1096579.Hotel-Information): Offers a seasonal outdoor pool, an indoor pool, and a 24-hour fitness center. [Renaissance St. Louis Airport Hotel](https://www.expedia.ca/St-Louis-Hotels-Renaissance-St-Louis-Airport-Hotel.h4672.Hotel-Information): Features an indoor pool, an outdoor pool, and buffet. ### What is there to see and do in Winchester? > Make a point to visit attractions like Lou Fusz Soccer Complex and Magic House - St. Louis Children's Museum. Discover sights such as Museum of Transportation, The Factory, and Route 66 State Park during your stay. ### When is the best time to book a hotel with a pool in Winchester? > You may want to consider an accommodation with an outdoor swimming pool if you will be visiting Winchester in the hottest months of July, August, or June when the average temperature is 76°F. Lodging with an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temp is 38°F. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [5 Star Hotels in Town and Country](https://www.expedia.ca/5Star-Town-And-Country-Hotels.s50-0-d6252549.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Ballwin](https://www.expedia.ca/Ballwin-Hotels-Beach-Hotel.0-0-d6354554-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Ballwin](https://www.expedia.ca/Ballwin-Hotels-Cheap-Hotels.0-0-d6354554-tCheapHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Ballwin](https://www.expedia.ca/Ballwin-Hotels-Romantic-Hotel.0-0-d6354554-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Ballwin Hotels](https://www.expedia.ca/Ballwin-Hotels.d6354554.Travel-Guide-Hotels) - [Vacation Homes in Ballwin](https://www.expedia.ca/Ballwin-Private-Vacation-Homes.d6354554-aaPrivateVacationHomes.Travel-Guide-Accommodation) - 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