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://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, CT from CA $140 - ![](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 16 - Nov 17](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-11-16&endDate=2025-11-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 17 - Nov 18](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-11-17&endDate=2025-11-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Hotels with a Pool ![Pool](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/31f305c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/31e09d21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/74bd7e00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/ebe022ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Bristol Bristol 9.6/10 Exceptional (157) "Would stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LARRY CA $178 CA $205 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/ecdb1729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/w531h370x4y0-37170d0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/936ec60f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/9c0a3e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Plainville Plainville 8.6/10 Excellent (905) "Yes, the room was clean. Staff was very nice and we look forward to our next stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Liza Marie CA $122 CA $140 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Hartford-Hotels-Fairfield-Inn-Suites-By-Marriott-Plainville.h9965.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/20124035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/d997675e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/e63c41d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/d9f37f65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Avon Old Farms Hotel Avon 8.4/10 Very good (1002) "Very nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alvero CA $162 CA $217 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/5dc7d6d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/a4ff04b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/1cbdfdde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/27e9804b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Hartford Avon Avon 8.8/10 Excellent (407) "Good hotel but expensive " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $154 CA $177 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Hartford-Hotels-Residence-Inn-By-Marriott-Hartford-Avon.h1074390.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/210000/203500/203496/a4febc34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/210000/203500/203496/07b77cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/210000/203500/203496/463bda09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/210000/203500/203496/83c04a55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Hartford-Farmington Farmington 8.4/10 Very good (1001) "great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) tatsiana CA $150 CA $173 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hartford-Hotels-Homewood-Suites-By-Hilton-Hartford-Farmington.h203496.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/0e1f3025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/111d9992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/01285f8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/393f3b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Hartford/Farmington Farmington 8.8/10 Excellent (1002) "Great breakfast buffet!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gina CA $168 CA $194 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/6349c6d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/50a90cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/52bc8d96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/d4318cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blackberry River Inn Norfolk 9.4/10 Exceptional (157) "Very good breakfast.excellent waiter.love the atmosphere." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marc CA $220 CA $253 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/5300/5265/1577fb22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch flat-screen TV with satellite channels, pay movies](https://images.trvl-media.com/lodging/1000000/10000/5300/5265/7baf880a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/5300/5265/de3a2b5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5300/5265/7a34507b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Bristol, Connecticut Bristol 9.0/10 Wonderful (1002) "Amazing stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marquise CA $206 CA $237 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hotel-Bristol.h5265.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/45cd21a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Ground Floor (Main Building)](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/db6c98da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/dbbfdf3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Woodside, Pet Friendly) | Terrace/patio](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/30d59e52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Interlaken Inn & Resort Lakeville 8.2/10 Very good (270) "Super clean and comfortable stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Padgett CA $233 CA $268 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Torrington-Hotels-Interlaken-Inn-Resort.h19679605.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/6326a611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/7e4b3c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/99af973d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/5cb24d7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Simsbury 1820 House Simsbury Center 9.2/10 Wonderful (1000) "Adorable bed and breakfast with a nice bar/restaurant. The staff were very accommodating. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chantel CA $243 CA $304 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Hartford-Hotels-Simsbury-1820-House.h42279.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=2025-11-30&endDate=2025-12-01®ionId=553248635975869849&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![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 "It was a good we spent time together so go ahead- keep-up Thanks " [](https://expedia.ca/Torrington-Hotels-Americas-Best-Value-Inn-Torrington-CT.h5738.Hotel-Information) ### Sheraton Hartford Hotel at Bradley Airport 10/10 Excellent "Aaa" [](https://expedia.ca/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.Hotel-Information) ### DoubleTree by Hilton Hotel Bristol, Connecticut 10/10 Excellent "Everything and everyone " [](https://expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hotel-Bristol.h5265.Hotel-Information) ### The Farmington Inn & Suites 10/10 Excellent "The room was nicely appointed. Surfaces were clean. But the towels were scratchy. Staff was very friendly and accommodating. I would definitely stay here again. " [](https://expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information) ### Hampton Inn & Suites Hartford/Farmington 10/10 Excellent "The hotel always smelled really nice! It was very clean." [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.Hotel-Information) ### Avon Old Farms Hotel 10/10 Excellent "This is a beautiful classic hotel with impeccable service. The grounds are so gorgeous! " [](https://expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) ### Fairfield Inn & Suites by Marriott Plainville 10/10 Excellent "Yes, the room was clean. Staff was very nice and we look forward to our next stay" [](https://expedia.ca/Hartford-Hotels-Fairfield-Inn-Suites-By-Marriott-Plainville.h9965.Hotel-Information) ### Homewood Suites by Hilton Hartford-Farmington 10/10 Excellent "Very good location for us. Room was very spacious with living, dining and sleeping areas." [](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 "Great stay, location, and service!!" [](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): Features a sauna, a seasonal outdoor pool, and buffet. [Sheraton Hartford Hotel at Bradley Airport](https://www.expedia.ca/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.Hotel-Information): Offers daily, an indoor pool, and complimentary wired internet access. [Avon Old Farms Hotel](https://www.expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information): Provides a snack bar/deli, an indoor pool, and free valet parking. [The Farmington Inn & Suites](https://www.expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information): Features a snack bar/deli, an indoor pool, and buffet. [Delamar West Hartford](https://www.expedia.ca/Hartford-Hotels-Delamar-West-Hartford.h18166744.Hotel-Information): Offers 2 bars, an indoor pool, and daily. ### 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 The Marina at Highland Lake, Burr Pond State Park, and Winchester Historical Society. ### 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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