Title: Book the Best Hotels with POOL in Cheshire in 2026 | 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) ![Castle Craig at Hubbard Park, Meriden, CT. easily replaceable sky. with a clean, classic view of the tower. Very recognizable image of this historic structure.](https://images.trvl-media.com/place/183057/92c74fd9-1a45-4931-a43e-251e181e803f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/183057/92c74fd9-1a45-4931-a43e-251e181e803f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2026-01-14&endDate=2026-01-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 15 - Jan 16](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2026-01-15&endDate=2026-01-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Cheshire hotels with a pool ![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) ![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) ![](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/9672e16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/9cda9029.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Cheshire - Southington by IHG [](https://www.expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) Southington 8.4/10 Very good (1,000 reviews) "Pool was nice, breakfast was very good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $137 CA $158 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/593124d6.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/d09d2b4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/49253eeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/0a1f1c83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heritage Hotel, Golf, Spa & Conference Center [](https://www.expedia.ca/Southbury-Hotels-Heritage-Hotel.h35389.Hotel-Information) Southbury 8.4/10 Very good (1,003 reviews) "Very nice, staff were excellent." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Philip CA $152 CA $199 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Southbury-Hotels-Heritage-Hotel.h35389.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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/d045ec83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, individually furnished](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/3627bf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/da165588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Southington by IHG [](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) Southington 8.6/10 Excellent (1,198 reviews) "Clean comfortable room, friendly staff, great breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Megan CA $124 CA $142 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/31f305c2.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) ![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/ebe022ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/10e91fff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Bristol [](https://www.expedia.ca/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information) Bristol 9.6/10 Exceptional (181 reviews) "Clean room, great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tamiya CA $180 CA $207 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information) ![Fitness facility](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/eba50eaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/ff093bb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/a12e56fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/0d731ede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt House Shelton [](https://www.expedia.ca/New-Haven-Hotels-HYATT-House-Shelton.h3482162.Hotel-Information) Shelton 8.4/10 Very good (1,006 reviews) "cleanliness and the people were pleasant at the desk as well as in the café area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) hartley CA $161 CA $185 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/New-Haven-Hotels-HYATT-House-Shelton.h3482162.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/b264062c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fountain](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/22690654.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) ### Avon Old Farms Hotel [](https://www.expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) Avon 8.4/10 Very good (1,000 reviews) "I love this hotel. Beds are so comfy, showers are hot with great water pressure, large bathrooms, nice amenities, friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann CA $165 CA $220 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/2f044af4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/b3db2b30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Jetted Tub](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/d9e2e7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/94c389ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus New England Inn & Suites [](https://www.expedia.ca/Hartford-Hotels-Best-Western-Plus-New-England-Inn-Suites.h922173.Hotel-Information) Berlin 8.6/10 Excellent (1,017 reviews) "Excellent Very warm staff Beds are very comfortable Coffee machine is such a great idea Breakfast was great " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark CA $121 CA $139 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Hartford-Hotels-Best-Western-Plus-New-England-Inn-Suites.h922173.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) ![Lobby](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/5af2dc31.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) ![Meeting facility](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/84719ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Milford [](https://www.expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Milford.h2473639.Hotel-Information) Milford 8.4/10 Very good (1,001 reviews) "Very nice hotel clean friendly convenient location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $132 CA $152 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Milford.h2473639.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979983/a45c48e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979983/95bf4352.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979983/cf46bed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily breakfast](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979983/4a7d934c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Orange New Haven [](https://www.expedia.ca/New-Haven-Hotels-Homewood-Suites-By-Hilton-Orange-New-Haven.h38979983.Hotel-Information) Orange 9.2/10 Wonderful (1,006 reviews) "Nice roomy room, clean, comfortable bed, plenty of hot water " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $145 CA $166 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/New-Haven-Hotels-Homewood-Suites-By-Hilton-Orange-New-Haven.h38979983.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/fd93f670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/6855e0e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/7d962b8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/f4aacb9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Executive Hotel Of New Haven - West Haven [](https://www.expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) West Haven 8.0/10 Very good (1,530 reviews) "Decent hotel for the price " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexa CA $133 CA $153 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.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=2026-01-28&endDate=2026-01-29®ionId=183057&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Cheshire Hotel Reviews ![Holiday Inn Express Southington by IHG](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2_y.jpg) ### Holiday Inn Express Southington by IHG 10/10 Excellent "The staff was kind and courteous from the moment we arrived. Our room was very clean and our breakfast was good as well. We would most likely return if in the area in the future." [](https://expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Hampton Inn by Hilton Shelton](https://images.trvl-media.com/lodging/1000000/210000/200400/200381/e6ef0843_y.jpg) ### Hampton Inn by Hilton Shelton 10/10 Excellent "Yes " [](https://expedia.ca/New-Haven-Hotels-Hampton-Inn-By-Hilton-Shelton.h200381.Hotel-Information) ![Hyatt Place Milford / New Haven](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg) ### Hyatt Place Milford / New Haven 10/10 Excellent "Yes" [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![Courtyard by Marriott Waterbury Downtown](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/c0e669e8_y.jpg) ### Courtyard by Marriott Waterbury Downtown 10/10 Excellent "The staff were great I had a problem with my first room and had to change rooms. I wasn’t happy about the inconvenience but overall my stay was good. The parking was a pain to far in the cold. " [](https://expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.Hotel-Information) ![Inn at Middletown](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/4e71c540_y.jpg) ### Inn at Middletown 10/10 Excellent "Staff was wonderful, lovely hotel" [](https://expedia.ca/Hartford-Hotels-Inn-At-Middletown.h6747876.Hotel-Information) ![Hampton Inn & Suites Hartford/East Hartford](https://images.trvl-media.com/lodging/3000000/2950000/2943100/2943093/5cf369a5_y.jpg) ### Hampton Inn & Suites Hartford/East Hartford 10/10 Excellent "Great place to stay. Right in the heart of Hartford. Bed was comfortable, room was clean, breakfast was good, and the staff were wonderful." [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-Suites-HartfordEast-Hartford.h2943093.Hotel-Information) ![Home2 Suites by Hilton East Haven New Haven](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/b5c018f9_y.jpg) ### Home2 Suites by Hilton East Haven New Haven 10/10 Excellent "Very good " [](https://expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.Hotel-Information) ![Hampton Inn & Suites Hartford/Farmington](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/393f3b68_y.jpg) ### Hampton Inn & Suites Hartford/Farmington 10/10 Excellent "Best egg/cheese omelets I've ever had in a budget breakfast buffet hotel. Fruit very good and fresh. Coffee good too. " [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.Hotel-Information) ![Hilton Garden Inn Hartford South/Glastonbury](https://images.trvl-media.com/lodging/1000000/990000/984900/984868/3109ce5b_y.jpg) ### Hilton Garden Inn Hartford South/Glastonbury 10/10 Excellent "The staff was very friendly, the hotel clean and comfortable. It was very nice to stay here with my dog especially during the holiday week. Thank you!" [](https://expedia.ca/Hartford-Hotels-Hilton-Garden-Inn-Hartford-SouthGlastonbury.h984868.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Cheshire? ### What is there to see and do in Cheshire? ### When is the best time to book a hotel with a pool in Cheshire? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Hotels near Brookside Park ](https://www.expedia.ca/Brookside-Park-Hotels.0-l553248621557919974-0.Travel-Guide-Filter-Hotels) - [B&B in Cheshire Historic District ](https://www.expedia.ca/Cheshire-Historic-District-Bed-And-Breakfast.d6346724-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Country Houses in Cheshire Historic District ](https://www.expedia.ca/Cheshire-Historic-District-Country-House.d6346724-aaCountryHouse.Travel-Guide-Accommodation) - [Guest Houses in Cheshire Historic District ](https://www.expedia.ca/Cheshire-Historic-District-Guest-Houses.d6346724-aaGuestHouses.Travel-Guide-Accommodation) - 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