Title: Book the Best Hotels with POOL in Cheshire in 2025 | Expedia.ca [Hotels in Cheshire](https://expedia.ca/Cheshire-Hotels.d183057.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.ca/Cheshire-Vacation-Rentals.d183057.Travel-Guide-VacationRentals)[Flights to Cheshire](https://expedia.ca/Cheap-Flights-To-Cheshire.d183057.Travel-Guide-Flights)[Cheshire Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire.d183057.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.ca/Cheshire.d183057.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/ab039a4411a79c16e7c533ffaba43069.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Tai Bui # Find Hotels with a Pool in Cheshire, CT from CA $137 - ![](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 Cheshire Hotels with a Pool Tonight [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-11-01&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-11-02&endDate=2025-11-03&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cheshire 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) ![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/ebe022ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/d26781d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Bristol Bristol 9.6/10 Exceptional (150) "Would stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LARRY CA $171 CA $197 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/ec5a48cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/d045ec83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/cb3d49ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Southington by IHG Southington 8.6/10 Excellent (1145) "Nice place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $132 CA $151 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/f224bafd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/d1cdaed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/3fa625b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/a84dbb59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection Southbury 8.4/10 Very good (1005) "Great stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Geraldine CA $160 CA $203 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Danbury-Hotels-Heritage-Hotel.h35389.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2080000/2078500/2078403/0494208e.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/3000000/2080000/2078500/2078403/e4131984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/3000000/2080000/2078500/2078403/0740f60a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/3000000/2080000/2078500/2078403/b6f421aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites New Haven - South - West Haven West Haven 8.4/10 Very good (1001) "Great breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elyse CA $120 CA $137 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/New-Haven-Hotels-Hampton-Inn-Suites-New-Haven-South-West-Haven.h2078403.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/95bfeb2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/412fe155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/0b53186c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (USD 16.95 per person)](https://images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/e45c4a80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham Southbury Southbury 8.2/10 Very good (1007) "Clean, nice, super convenient. Great restaurants in the area. Beautiful setting." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Courtney CA $130 CA $149 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Danbury-Hotels-Wyndham-Southbury.h15651820.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) ![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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/01d5897d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Plainville Plainville 8.6/10 Excellent (903) "Great stay would and will stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $122 CA $140 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hartford-Hotels-Fairfield-Inn-Suites-By-Marriott-Plainville.h9965.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/w1703h1271x0y0-b305e0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/a3c0d287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/e12904c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/33420ad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Cheshire - Southington by IHG Southington 8.2/10 Very good (1004) "The rooms were clean and staff were very attentive." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rodger CA $140 CA $161 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/84e6e761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/657809e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/ff6d89d5.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/1000000/930000/922200/922173/5ef2aedd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus New England Inn & Suites Berlin 8.6/10 Excellent (1014) "arrived at 9:30 pm as a single woman and felt very safe " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melanie CA $134 CA $154 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Hartford-Hotels-Best-Western-Plus-New-England-Inn-Suites.h922173.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/24000000/23520000/23512500/23512415/c13ca28b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/24000000/23520000/23512500/23512415/28afb7d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23520000/23512500/23512415/ef60c25f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23520000/23512500/23512415/5b8179ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Rocky Hill - Hartford South Rocky Hill 9.2/10 Wonderful (754) "Great stay. Easy parking. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $144 CA $166 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hartford-Hotels-Hampton-Inn-Suites-Rocky-Hill-Hartford-South.h23512415.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/ba785aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, Tempur-Pedic beds, individually furnished](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/5b9f8936.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/b8a2e8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/268b5ae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Milford Milford 8.4/10 Very good (1001) "This hotel is wonderful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberto CA $142 CA $164 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Milford.h2473639.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=2025-11-15&endDate=2025-11-16®ionId=183057&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Cheshire Hotel Reviews ![Wyndham Southbury](//images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/412fe155_y.jpg) ### Wyndham Southbury 10/10 Excellent "Yes" [](https://expedia.ca/Danbury-Hotels-Wyndham-Southbury.h15651820.Hotel-Information) ![Best Western Executive Hotel Of New Haven - West Haven](//images.trvl-media.com/lodging/1000000/30000/23300/23217/b63e42e2_y.jpg) ### Best Western Executive Hotel Of New Haven - West Haven 10/10 Excellent "My 3, well (2½) day stay was overall not bad untill........ On My 2 day of booking the room i was asked by the the woman with a clip board who im assuming was the head of in house keeping if i was staying for another day which i had told her yes and she asked would i be needing house keeping to go in my room which i replied no alls i need is fresh towels......" [](https://expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Holiday Inn Express Southington by IHG](//images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2_y.jpg) ### Holiday Inn Express Southington by IHG 10/10 Excellent "Room was immaculate; the staff was friendly and prompt Breakfast area neatly arranged. Will go back for sure" [](https://expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Hilton Garden Inn Shelton](//images.trvl-media.com/lodging/1000000/290000/287700/287687/18ff21f4_y.jpg) ### Hilton Garden Inn Shelton 10/10 Excellent "the room was very clean and fragrant" [](https://expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Shelton.h287687.Hotel-Information) ![Best Western Hartford Hotel & Suites](//images.trvl-media.com/lodging/1000000/20000/12200/12156/cfbe36c4_y.jpg) ### Best Western Hartford Hotel & Suites 10/10 Excellent "Great Place, recommend to others." [](https://expedia.ca/Hartford-Hotels-Best-Western-Hartford-Hotel-Suites.h12156.Hotel-Information) ![Hyatt Place Milford / New Haven](//images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg) ### Hyatt Place Milford / New Haven 10/10 Excellent " Very helpful with a 2nd party reservation " [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![La Quinta Inn & Suites by Wyndham New Haven](//images.trvl-media.com/lodging/1000000/10000/1300/1241/e8cbddf6_y.jpg) ### La Quinta Inn & Suites by Wyndham New Haven 8/10 Good "Rooms are good, building under renovation at the moment." [](https://expedia.ca/New-Haven-Hotels-La-Quinta-Inn-Suites-By-Wyndham-New-Haven.h1241.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Cheshire? > [Cheshire Welcome Inn](https://www.expedia.ca/New-Haven-Hotels-Cheshire-Welcome-Inn.h1896545.Hotel-Information): Hotel located near Connecticut Convention Center. Features buffet, a seasonal outdoor pool, and free self parking. [The Capitol Hotel](https://www.expedia.ca/Hartford-Hotels-The-Capitol-Hotel.h6777.Hotel-Information): Provides a snack bar/deli, a seasonal outdoor pool, and buffet. [Motel 6 New Haven - Branford, CT](https://www.expedia.ca/New-Haven-Hotels-Motel-6-New-Haven-Branford.h50320.Hotel-Information): Offers a snack bar/deli, an indoor pool, and complimentary wired internet access. [Best Western Hartford Hotel & Suites](https://www.expedia.ca/Hartford-Hotels-Best-Western-Hartford-Hotel-Suites.h12156.Hotel-Information): Offers full, a pool, and free self parking. [Extended Stay America Suites Hartford Farmington](https://www.expedia.ca/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.Hotel-Information): Hotel located near Quinnipiac University. Features buffet, an indoor pool, and complimentary wired internet access. ### What is there to see and do in Cheshire? > Spend some time experiencing the great outdoors at Drazen Orchards and Bartlem Park. Discover sights such as Barker Character, Comic and Cartoon Museum, Cheshire Hollow Farm, and Maplecroft Plaza Shopping Center during your stay. You'll also discover lots of options for restaurants in Cheshire. ### When is the best time to book a hotel with a pool in Cheshire? > You may want to consider a place to stay that has an outdoor pool if you will be visiting Cheshire in the hottest months of July, August, or June when the average temperature is 70°F. 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