Title: Book the Best Hotels with POOL in Winchester in 2025 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d183815.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d183815.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d183815.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d183815.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Winchester, OH from CA $96 - ![](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 [Nov 8 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2025-11-08&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 9 - Nov 10](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2025-11-09&endDate=2025-11-10&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Hotels with a Pool ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/50000/42800/42751/4d24e63d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42800/42751/def57d46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/50000/42800/42751/2a9ff762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/50000/42800/42751/4a2d6cba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Seaman Seaman 7.4/10 Good (288) "Nice room friendly staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles CA $120 CA $132 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Hillsboro-Hotels-Quality-Inn.h42751.Hotel-Information) ![Standard Penthouse, Pool View | Terrace/patio](https://images.trvl-media.com/lodging/109000000/108730000/108721700/108721615/69d05e53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108730000/108721700/108721615/fd95e93e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108730000/108721700/108721615/w712h1265x0y12-ec403e11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Penthouse, Pool View | Private kitchen](https://images.trvl-media.com/lodging/109000000/108730000/108721700/108721615/2ca35418.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beverly hills inn Aberdeen 8.6/10 Excellent (140) "The staff is very sweet, room was very clean and comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keerson [](https://www.expedia.ca/Aberdeen-Hotels-Beverly-Hills-Inn.h108721615.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/50000/42800/42776/3fecbe94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/42800/42776/2ed795d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/50000/42800/42776/a6618963.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/50000/42800/42776/0ea60812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Hillsboro Hillsboro 7.2/10 Good (274) "Staff was very kind and friendly, hotel was clean, maintained. Convenient location to the festival we went to and central to shopping stores (Walmart, 5Below, Dollar stores, Marshalls, Tmobile, Krogers, Goodwill, Aldi being built, etc...) Will definitely book with them again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia CA $134 CA $147 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Hillsboro-Hotels-Days-Inn-By-Wyndham-Hillsboro.h42776.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/330000/327900/327877/2279414d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/330000/327900/327877/2c0e7fee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/1000000/330000/327900/327877/fb384e7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free continental breakfast on weekends](https://images.trvl-media.com/lodging/1000000/330000/327900/327877/9f1bcd38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Countryside Inn & Suites Mount Orab 7.2/10 Good (542) "Great place, just the breakfast could've been better " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SHAWN CA $121 CA $137 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hillsboro-Hotels-Countryside-Inn-Suites.h327877.Hotel-Information) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/12000000/11270000/11268300/11268211/c5befd8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, free toiletries, towels, soap](https://images.trvl-media.com/lodging/12000000/11270000/11268300/11268211/5e4ecdbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed](https://images.trvl-media.com/lodging/12000000/11270000/11268300/11268211/8ecf6ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, free toiletries, towels, soap](https://images.trvl-media.com/lodging/12000000/11270000/11268300/11268211/1deab68d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hillsboro Inn & Suites Hillsboro 6.4/10 (38) "There was no office , just a window, nothing for kids , wasn't to bad but wouldn't revisit this place. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deniese CA $101 CA $111 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Hillsboro-Hotels-Cedar-Hill-Motel.h11268211.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/16000000/15590000/15589500/15589406/4c159e65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15590000/15589500/15589406/3a92440f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, City View](https://images.trvl-media.com/lodging/16000000/15590000/15589500/15589406/d9c3cce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, River View | View from room](https://images.trvl-media.com/lodging/16000000/15590000/15589500/15589406/86b64341.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### French Quarter Inn Maysville 8.8/10 Excellent (758) "Enjoyed the historical, Southern comfort vibe." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine CA $279 CA $311 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Maysville-Hotels-French-Quarter-Inn.h15589406.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/123000000/122100000/122099600/122099546/a811f193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122100000/122099600/122099546/0855e65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/123000000/122100000/122099600/122099546/9a4f1674.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122100000/122099600/122099546/6d6b9611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Cornerstone Retreat Upstairs - Hot Tub, Sauna, Grill, Fire Pit, Massage Hillsboro CA $334 CA $380 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Lynchburg-Hotels-Country-Cornerstone-Retreat-Upstairs.h122099546.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/116000000/115560000/115554900/115554816/0e218996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115560000/115554900/115554816/cc7c5bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115560000/115554900/115554816/20831dc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, stereo](https://images.trvl-media.com/lodging/116000000/115560000/115554900/115554816/33289191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Cornerstone Retreat - Game Room, Theater, Hot Tub, Massage, Sauna, BBQ Hillsboro 10/10 Exceptional (2) "The property was perfect for our family weekend getaway. The game room, massage chairs, theater room and hot tub were huge hits. The house was very well stocked with everything we needed to cook full meals. Keith answered every question we had promptly and they had planned for everything including a spare coffee maker when the primary one didn’t work. It’s secluded and quiet for restful and relaxing time away. There was even a on site charger for our EV. We would definitely stay again!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $491 CA $991 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Hillsboro-Hotels-Country-Cornerstone-Retreat.h115554816.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17100/17042/717c2db7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17100/17042/a3c5644e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/17100/17042/a75582c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/20000/17100/17042/5a32ce9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Maysville Maysville 6.0/10 (181) "Room could use updates but not bad for the night " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darian CA $86 CA $96 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Maysville-Hotels-Quality-Inn-Maysville-Area.h17042.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=2025-11-22&endDate=2025-11-23®ionId=183815&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![Days Inn by Wyndham Hillsboro](//images.trvl-media.com/lodging/1000000/50000/42800/42776/0ea60812_y.jpg) ### Days Inn by Wyndham Hillsboro 10/10 Excellent "Gray bang for your buck with clean rooms and super nice staff. Would absolutely stay there again. " [](https://expedia.ca/Hillsboro-Hotels-Days-Inn-By-Wyndham-Hillsboro.h42776.Hotel-Information) ![Countryside Inn & Suites](//images.trvl-media.com/lodging/1000000/330000/327900/327877/2c0e7fee_y.jpg) ### Countryside Inn & Suites 10/10 Excellent "This is my second time staying here. The room is very clean. I have no complaints at all. I did not have breakfast." [](https://expedia.ca/Hillsboro-Hotels-Countryside-Inn-Suites.h327877.Hotel-Information) ![French Quarter Inn](//images.trvl-media.com/lodging/16000000/15590000/15589500/15589406/w1000h451x0y0-8ba0d251_y.jpg) ### French Quarter Inn 10/10 Excellent "The hotel was great as we were in the town to do family research and it was quiet and great for what we were doing." [](https://expedia.ca/Maysville-Hotels-French-Quarter-Inn.h15589406.Hotel-Information) ![Days Inn by Wyndham Maysville Kentucky](//images.trvl-media.com/lodging/1000000/30000/25500/25466/032fdf94_y.jpg) ### Days Inn by Wyndham Maysville Kentucky 10/10 Excellent "It was all about the people and how they worked together with us to render the best stay possible. Informed, knowledgeable and compassionate!" [](https://expedia.ca/Maysville-Hotels-Days-Inn-By-Wyndham-Maysville-Kentucky.h25466.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/20000/17100/17042/5a32ce9b_y.jpg) ### Quality Inn 10/10 Excellent "Cleanliness, great staff friendly no great I mean great, dining nearby. Great shopping nearby. Great." [](https://expedia.ca/Maysville-Hotels-Quality-Inn-Maysville-Area.h17042.Hotel-Information) ![Quality Inn Seaman](//images.trvl-media.com/lodging/1000000/50000/42800/42751/def57d46_y.jpg) ### Quality Inn Seaman 10/10 Excellent "We visited 3 days as a family of 4 and never did they replace the towels, empty trash nor straighten beds. We had to ask for extra coffee for the morning (staff politely supplied) and the coffee machine in the breakfast area did not have regular coffee, just decaf. The room smelled musty and the wall air conditioner was not very cooling." [](https://expedia.ca/Hillsboro-Hotels-Quality-Inn.h42751.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Winchester? > [Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !](https://www.expedia.ca/Hillsboro-Hotels-Newly-Built-Rustic-3-Bedroom-Cabin-With-A-One-Acre-Fishing-Lake.h29913121.Hotel-Information): Hotel, 1-minute walk from Ohio River Valley. Offers 2 restaurants, a seasonal outdoor pool, and free self parking. [Beverly hills inn](https://www.expedia.ca/Aberdeen-Hotels-Beverly-Hills-Inn.h108721615.Hotel-Information): Provides continental, an indoor pool, and free self parking. [Countryside Inn & Suites](https://www.expedia.ca/Hillsboro-Hotels-Countryside-Inn-Suites.h327877.Hotel-Information): Offers daily, a seasonal outdoor pool, and free self parking. [Days Inn by Wyndham Maysville Kentucky](https://www.expedia.ca/Maysville-Hotels-Days-Inn-By-Wyndham-Maysville-Kentucky.h25466.Hotel-Information): Hotel, 1-minute walk from Ohio River Valley. Features daily, a seasonal outdoor pool, and free self parking. [Days Inn by Wyndham Hillsboro](https://www.expedia.ca/Hillsboro-Hotels-Days-Inn-By-Wyndham-Hillsboro.h42776.Hotel-Information): Hotel located near Ohio River Valley. Offers free self parking, an indoor pool, and complimentary wireless internet access. ### What is there to see and do in Winchester? > The picturesque setting of Rocky Fork Lake State Park and Rocky Fork Lake showcase the area's natural beauty. During your stay, check out sights such as Serpent Mound, Hillsboro Elks Country Club, and Rocky Fork State Park. ### When is the best time to book a hotel with a pool in Winchester? > You may want to think about a place to stay that has an outdoor pool if you're planning to visit Winchester in the warmest months of July, August, or June when the average temperature is 72°F. Lodging offering an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temp is 37°F. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - More ways to book - [5 Star Hotels in Peebles](https://www.expedia.ca/5Star-Peebles-Hotels.s50-0-d6195740.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Sardinia](https://www.expedia.ca/5Star-Sardinia-Hotels.s50-0-d553248634983507551.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Aberdeen](https://www.expedia.ca/Aberdeen-Hotels-Cheap-Hotels.0-0-d6344064-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Aberdeen](https://www.expedia.ca/Aberdeen-Hotels-Hotel-With-Pool.0-0-d6344064-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Aberdeen](https://www.expedia.ca/Aberdeen-Hotels-Hotels-With-Balconies.0-0-d6344064-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Golf Hotels in Batavia](https://www.expedia.ca/Batavia-Hotels-Golf-Hotel.0-0-d6034563-tGolfHotel.Travel-Guide-Filter-Hotels) - 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