Title: Book the Best Hotels with POOL in Winchester in 2025 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d553248635975869849.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d553248635975869849.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d553248635975869849.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d553248635975869849.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, CT ![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=553248635975869849&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=553248635975869849&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=553248635975869849&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=553248635975869849&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 ## Top Winchester Hotel Reviews ![Fairfield Inn & Suites by Marriott Plainville](//images.trvl-media.com/lodging/1000000/10000/10000/9965/01d5897d_y.jpg) ### Fairfield Inn & Suites by Marriott Plainville 10/10 Excellent "Wonderful stay except the pool was out of order and no hot tub or steam room" [](https://expedia.ca/Hartford-Hotels-Fairfield-Inn-Suites-By-Marriott-Plainville.h9965.Hotel-Information) ![Sheraton Hartford Hotel at Bradley Airport](//images.trvl-media.com/lodging/1000000/10000/4700/4632/c8edc11d_y.jpg) ### Sheraton Hartford Hotel at Bradley Airport 10/10 Excellent "Convenient " [](https://expedia.ca/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.Hotel-Information) ![Hampton Inn & Suites Hartford/Farmington](//images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/393f3b68_y.jpg) ### Hampton Inn & Suites Hartford/Farmington 10/10 Excellent "Nicely appointed room - mini suite. Dog friendly. Comfy and clean" [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.Hotel-Information) ![Americas Best Value Inn Torrington CT](//images.trvl-media.com/lodging/1000000/10000/5800/5738/a9b48332_y.jpg) ### Americas Best Value Inn Torrington CT 10/10 Excellent "The staff was very respectful the room was celan and they were understanding of the circumstance i registered for the rolm under" [](https://expedia.ca/Torrington-Hotels-Americas-Best-Value-Inn-Torrington-CT.h5738.Hotel-Information) ![The Farmington Inn & Suites](//images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a_y.jpg) ### The Farmington Inn & Suites 10/10 Excellent "Great staff, very helpful. Good location." [](https://expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information) ![DoubleTree by Hilton Hotel Bristol, Connecticut](//images.trvl-media.com/lodging/1000000/10000/5300/5265/7a34507b_y.jpg) ### DoubleTree by Hilton Hotel Bristol, Connecticut 10/10 Excellent "It was next to the amusement park and food options. The pool and hot tub were great " [](https://expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hotel-Bristol.h5265.Hotel-Information) ![Residence Inn by Marriott Hartford Avon](//images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/5dc7d6d4_y.jpg) ### Residence Inn by Marriott Hartford Avon 10/10 Excellent "Staff was great" [](https://expedia.ca/Hartford-Hotels-Residence-Inn-By-Marriott-Hartford-Avon.h1074390.Hotel-Information) ![Homewood Suites by Hilton Hartford-Farmington](//images.trvl-media.com/lodging/1000000/210000/203500/203496/4f26a2b3_y.jpg) ### Homewood Suites by Hilton Hartford-Farmington 10/10 Excellent "Good breakfast for the hotel class. " [](https://expedia.ca/Hartford-Hotels-Homewood-Suites-By-Hilton-Hartford-Farmington.h203496.Hotel-Information) ![Simsbury Inn](//images.trvl-media.com/lodging/1000000/20000/16800/16756/ceb52ab8_y.jpg) ### Simsbury Inn 10/10 Excellent "The staff was super friendly. Our room was large and immaculate. The free breakfast had more items than I usually eat going out for breakfast (not and cold items). The pool and whirlpool were awesome, had great music playing and no one was there. Will definitely go back." [](https://expedia.ca/Weatogue-Hotels-Simsbury-Inn.h16756.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Winchester? > [Extended Stay America Suites Hartford Farmington](https://www.expedia.ca/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.Hotel-Information): Provides a sauna, a seasonal outdoor pool, and buffet. [Avon Old Farms Hotel](https://www.expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information): Offers daily, an indoor pool, and complimentary wired internet access. [The Farmington Inn & Suites](https://www.expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information): Provides a snack bar/deli, an indoor pool, and buffet. [Sheraton Hartford Hotel at Bradley Airport](https://www.expedia.ca/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.Hotel-Information): Features a snack bar/deli, a pool, and daily. [Delamar West Hartford](https://www.expedia.ca/Hartford-Hotels-Delamar-West-Hartford.h18166744.Hotel-Information): Offers a snack bar/deli, an indoor pool, and free valet parking. ### What is there to see and do in Winchester? > Make a point to visit attractions like Highland Lake and Laurel Lanes. During your stay, check out sights such as Burr Pond State Park, Platt Hill State Park, and The Marina at Highland Lake. ### When is the best time to book a hotel with a pool in Winchester? > Taking into account the local weather in Winchester can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Cheap Hotels in Barkhamsted](https://www.expedia.ca/Barkhamsted-Hotels-Cheap-Hotels.0-0-d6359343-tCheapHotels.Travel-Guide-Filter-Hotels) - [Motels in Barkhamsted](https://www.expedia.ca/Barkhamsted-Motels.d6359343-aaMotels.Travel-Guide-Accommodation) - [Apartments in City Meadow Boardwalk](https://www.expedia.ca/City-Meadow-Boardwalk-Apartments.d903594079282372608-aaApartments.Travel-Guide-Accommodation) - [Cottages in City Meadow Boardwalk](https://www.expedia.ca/City-Meadow-Boardwalk-Cottages.d903594079282372608-aaCottages.Travel-Guide-Accommodation) - [Farmstay in Colebrook](https://www.expedia.ca/Colebrook-Agritourism.d6125522-aaAgritourism.Travel-Guide-Accommodation) - [Cheap Hotels in Colebrook](https://www.expedia.ca/Colebrook-Hotels-Cheap-Hotels.0-0-d6125522-tCheapHotels.Travel-Guide-Filter-Hotels) - 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