Title: Book the Best Hotels with POOL in Cheshire in 2025 | Expedia.ca [Hotels in Cheshire](https://expedia.ca/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.ca/Cheshire-Vacation-Rentals.d6005398.Travel-Guide-VacationRentals)[Cheshire Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire.d6005398.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.ca/Cheshire.d6005398.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/03b3e41380b5e881ce17dedb6946d4ac.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ed Gaffny # Find Hotels with a Pool in Cheshire, MA from CA $124 ![](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 [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-19&endDate=2025-10-20&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-20&endDate=2025-10-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cheshire Hotels with a Pool ![Indoor pool](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b548733b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/c0933de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/754813dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires Lenox 9.2/10 Wonderful (5) "New hotel very nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joel CA $189 CA $211 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/074b6c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (908) "Enjoyable stay. Staff were very nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Claire CA $144 CA $161 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/7062b6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/5a6f7f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/69e559b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Lenox Lenox 7.6/10 Good (813) "We enjoyed our stay. It's basic but clean and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kit Ping CA $111 CA $124 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/52cb5a56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/69831a98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Suite, 1 King Bed, Patio | Living area](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/5e670f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 3 Bedrooms, Mountainside | Living area](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/2f0dc604_edited_9c5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Springs Motel New Ashford 9.2/10 Wonderful (80) "The Springs Motel was a delight! Something away from the boring, staple type of hotel. The staff was so friendly and welcoming. The coffee and breakfast is a great touch! Can't wait to go back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tricia CA $144 CA $158 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/New-Ashford-Hotels-The-Springs-Motel.h95124564.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/caece0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/44727a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/5062d555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/af22be9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Corner Motel Williamstown 9.2/10 Wonderful (876) "Very nice staff, nice breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kerri CA $105 CA $124 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/53ddce52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/b51475ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/74865ec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Mountain Lodge Pittsfield 9.0/10 Wonderful (716) "Great stay, perfect " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lawrence CA $131 CA $177 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Indoor pool, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/ceca8706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/e55e7242.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/3e2c75da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Berkshires-Lenox Lenox 9.2/10 Wonderful (1003) "Very clean, nice amenities , great location!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin CA $167 CA $187 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/219cd416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/483e190d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/049cb490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deep soaking bathtub](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/14870b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Inn Lee 7.6/10 Good (407) "That can be reserved at any time" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Felicita CA $136 CA $152 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Lee-Hotels-Sunset-Inn.h3025486.Hotel-Information) ![Indoor pool, outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/18127ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/16150550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/64adfbe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Village in the Berkshires Williamstown 8.8/10 Excellent (2081) "Clean and great pool and hot tub facilities " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alyce CA $129 CA $159 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/92f285fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/c64cd286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds | View from room](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/44b0e4d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/df923dad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maple Terrace Motel Williamstown 9.6/10 Exceptional (581) "Excellent place. Bountiful view. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tania CA $139 CA $155 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.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=2025-11-02&endDate=2025-11-03®ionId=6005398&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Cheshire Hotel Reviews ![Vacation Village in the Berkshires](//images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Front desk was friendly and helpful. Plenty of parking near our specific unit. Our room was clean, spacious, and very comfortable. The pool and hot tub area were clean and had plenty of towels to use. This was our first time here and we will definitely come back. " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "In a very nice annex suite." [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Enjoyable stay. Staff were very nice. " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Staff was very welcoming and friendly! They provided great tips on restaurants and things to do in are." [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](//images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Great stay-- would stay here again-- safe, nice welcome from Cameron at front desk, room was clean and cozy. Bed was very comfortable. Didn't have breakfast. I usually stay in Pittsfield at a hotel that has given me a discount since March when my mother was put into a nursing home. I normally try to come down twice a month from CNY--needless to say it is expensive for me.. Random question-- do you offer discounts?" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "Clean room, nice view" [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Howard Johnson by Wyndham Lenox](//images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg) ### Howard Johnson by Wyndham Lenox 10/10 Excellent "Good for the one night drive through! " [](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Jiminy Peak Mountain Resort](//images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830_y.jpg) ### Jiminy Peak Mountain Resort 10/10 Excellent "This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay." [](https://expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](//images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "Felt comfortable and safe. Nice pool and gym facility." [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Cheshire? > [Harbour House Inn](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information): Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. [Vacation Village in the Berkshires](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information): Provides free self parking, an indoor pool, and complimentary wireless internet access. [Hotel Downstreet, an Ascend Collection Hotel](https://www.expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information): Features free self parking, an indoor pool, and complimentary wireless internet access. [Berkshire Mountain Lodge](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information): Features a health club, an indoor pool, and complimentary wired internet access. [Berkshires Untold](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information): Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli. ### What is there to see and do in Cheshire? > Take in the natural beauty with a stop at Mount Greylock State Reservation. Discover sights such as St Mary's of the Assumption Church, Mount Greylock State Reservation Visitor Center, and Mount Greylock during your stay. ### When is the best time to book a hotel with a pool in Cheshire? > Taking into account the local weather in Cheshire is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Farmstay in Adams](https://www.expedia.ca/Adams-Agritourism.d6005393-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Adams](https://www.expedia.ca/Adams-Apart-Hotels.d6005393-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Adams](https://www.expedia.ca/Adams-Bed-And-Breakfast.d6005393-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Adams](https://www.expedia.ca/Adams-Chalets.d6005393-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Adams](https://www.expedia.ca/Adams-Guest-Houses.d6005393-aaGuestHouses.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Adams](https://www.expedia.ca/Adams-Hotels-Beach-Hotel.0-0-d6005393-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Adams](https://www.expedia.ca/Adams-Hotels-Cheap-Hotels.0-0-d6005393-tCheapHotels.Travel-Guide-Filter-Hotels) - 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