Title: TOP Hotels with Pools in The Berkshires, MA for 2025 - The Berkshires Hotels with a Pool | Expedia.co.uk [The Berkshires Travel Guide](https://expedia.co.uk/The-Berkshires.dx6047665)[Hotels in The Berkshires](https://expedia.co.uk/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[Holiday Rentals in The Berkshires](https://expedia.co.uk/The-Berkshires-Holiday-Rentals.d6047665.Travel-Guide-HolidayRentals)[Flights to The Berkshires](https://expedia.co.uk/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[The Berkshires Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-The-Berkshires.d6047665.Car-Hire-Guide)[The Berkshires Holidays](https://expedia.co.uk/The-Berkshires.d6047665.Holidays-City-Breaks) ![The Berkshires featuring flowers](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/71000/71831-The-Berkshires.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Pool in The Berkshires, MA ![price find illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.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 Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![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 The Berkshires Hotels with Pool Tonight [5 Oct - 6 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-10-05&endDate=2025-10-06&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [6 Oct - 7 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-10-06&endDate=2025-10-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [10 Oct - 12 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top The Berkshires Hotels with Pool ![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) ![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) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Village in the Berkshires Williamstown 8.6/10 Excellent (2034) "Really nice place at a reasonable price" [](https://www.expedia.co.uk/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/c5ac23bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Room, 3 Bedrooms (Grand Summit Resort) | In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/9a9839ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/effe663b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/fea584b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mount Snow Grand Summit Resort West Dover 8.6/10 Excellent (229) "Great place to stay!" £126 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/West-Dover-Hotels-Mount-Snow-Grand-Summit-Resort.h663170.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) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/f450d89a.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) ![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) ### Berkshire Mountain Lodge Pittsfield 9.0/10 Wonderful (671) "Very convenient set up of both room and kitchen, resort very easy to navigate. " £94 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b548733b.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) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/c0933de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires Lenox 9.2/10 Wonderful (5) "New hotel very nice" £126 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/a2e409f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down duvets, minibar](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/b42c4262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/549437da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/9aaa75ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Prospect Berkshires Egremont 9.0/10 Wonderful (7) "Gorgeous thoughtfully designed cabins with so many amenities/activities. Cliff house restaurant was delicious. Perfect getaway. " £267 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.Hotel-Information) ![Outdoor pool, pool loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Main Inn Queen) | 1 bedroom, Frette Italian sheets, hypo-allergenic bedding, desk](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/3ac2703b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property – evening/night](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/4d2e9eec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds (Main Inn) | 1 bedroom, Frette Italian sheets, hypo-allergenic bedding, desk](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/5f2e6b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn Stockbridge 8.8/10 Excellent (1004) "great place have stayed several times, and hope to return." £164 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Indoor pool, open 8:00 AM to 10:00 PM, pool 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) ![One King Bed, Non-Smoking, Accessible | View from room](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/5d049cdd.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 (1000) "Very clean, nice amenities , great location!!" £112 includes taxes & fees 1 Nov - 2 Nov [](https://www.expedia.co.uk/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/4417504a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/ae684309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms | 2 bedrooms, Frette Italian sheets, premium bedding, down duvets](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Extended Stay) | 2 bedrooms, Frette Italian sheets, premium bedding, down duvets](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/c71b3d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Porches Inn at Mass MoCA North Adams 9.4/10 Exceptional (425) "Great hotel, lovely pool and hot tub. We got upgraded to a suite!" £178 includes taxes & fees 5 Nov - 6 Nov [](https://www.expedia.co.uk/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/439bea3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 1 King Bed with Sofa bed, Kitchen | Private kitchen | Fridge, microwave](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/f2112a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Apartment, 1 Bedroom, Kitchen | Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/0e6d6310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/5ca030cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Knotty Pine Bennington 9.0/10 Wonderful (2) "Very quiet. Evening staff efficient and helpful upon arrival. Breakfast was posted to start at 7 AM but food and drink was not ready. Left without breakfast. " £125 includes taxes & fees 23 Oct - 24 Oct [](https://www.expedia.co.uk/Bennington-Hotels-Knotty-Pine.h119106200.Hotel-Information) ![Indoor pool, open 6:00 AM to 10 PM, pool loungers](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/ecbe7d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/5e762248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/a866db4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/433bbf3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Downstreet, an Ascend Collection Hotel North Adams 8.8/10 Excellent (1000) "Property was very clean and view of mountain from window was awesome beds very comfortable and loved the hot tub and pool" £120 includes taxes & fees 5 Nov - 6 Nov [](https://www.expedia.co.uk/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.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.co.uk/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20®ionId=6047665&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top The Berkshires Hotel Reviews ![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 "Very nice!" [](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.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 "Great place! Food excellent ss well!" [](https://expedia.co.uk/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](//images.trvl-media.com/lodging/1000000/900000/892300/892229/4c557ede_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Comfortable, quiet and in a great location" [](https://expedia.co.uk/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![The Porches Inn at Mass MoCA](//images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "Great place to spend an autumn night." [](https://expedia.co.uk/North-Adams-Hotels-The-Porches-Inn.h7662392.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.co.uk/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.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 "Totally perfect for mass mocha" [](https://expedia.co.uk/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.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 "Cool" [](https://expedia.co.uk/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - More ways to book - [3 Star Hotels in Great Barrington](https://www.expedia.co.uk/3Star-Great-Barrington-Hotels.s30-0-d110336.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Chester](https://www.expedia.co.uk/4Star-Chester-Hotels.s40-0-d6005399.Travel-Guide-Filter-Hotels) - 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