Title: Book the Best Hotels with POOL in Hinsdale in 2026 | Expedia.ca [Hotels in Hinsdale](https://expedia.ca/Hinsdale-Hotels.d6005406.Travel-Guide-Hotels)[Vacation Rentals in Hinsdale](https://expedia.ca/Hinsdale-Vacation-Rentals.d6005406.Travel-Guide-VacationRentals)[Hinsdale Car Rentals](https://expedia.ca/Car-Rentals-In-Hinsdale.d6005406.Car-Rental-Guide)[Hinsdale Vacation Packages](https://expedia.ca/Hinsdale.d6005406.Destination-Travel-Guides) ![Had to wait on the light to get just right...totality worth it!!! #InStone](https://images.trvl-media.com/place/6005406/994d4472-5b99-4b6b-8148-12426b4c9b53.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Janine Edmondson ![](https://images.trvl-media.com/place/6005406/994d4472-5b99-4b6b-8148-12426b4c9b53.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 Hinsdale Hotels with a Pool Tonight [Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=6005406&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=6005406&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=6005406&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=6005406&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Hinsdale 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) ![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/06dae0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) Lenox 9.8/10 Exceptional (16 reviews) "Spotless rooms and the friendliest service at the front desk! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $193 CA $215 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/9ac40a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/be126a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/e2e7e72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) Great Barrington 8.8/10 Excellent (719 reviews) "We stay here every year and it never disappoints " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $148 CA $166 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3f4a1adf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/8cd694d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/dbcc78d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) Lenox 9.2/10 Wonderful (1,003 reviews) "Everything was great! " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Daphne CA $129 CA $144 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/91284a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/207845f4.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) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a97806ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) Pittsfield 8.0/10 Very good (1,000 reviews) "Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $136 CA $152 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/3c0625c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Villa, 3 Bedrooms](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/5aedd4f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Villa, 3 Bedrooms](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/24f01653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) South Lee 9.0/10 Wonderful (818 reviews) "We had a great stay! Karaoke in the bar was a blast!! Great little condo!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie CA $148 CA $192 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Indoor pool, open 6:00 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/70229688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/185ae7e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/1294364a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/39644ba9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Downstreet, an Ascend Collection Hotel [](https://www.expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) North Adams 8.8/10 Excellent (1,000 reviews) "Staff was pleasant and helpful, room spacey and all immaculate ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $174 CA $194 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Gazebo](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/6df66696.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/c0f1d776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/7aabad6c.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) ### Cozy Corner Motel [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) Williamstown 9.2/10 Wonderful (890 reviews) "Excellent service and a beautifully decorated property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ivana CA $96 CA $114 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) ![Indoor pool, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/601f8574.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/2000000/1930000/1927100/1927087/320c2d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/d8fde5b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One King Studio Sofabed Non Smoking | View from room](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/w3837h2559x0y0-777976aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Berkshires-Lenox [](https://www.expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) Lenox 9.2/10 Wonderful (1,000 reviews) "The room and amenities were amazing. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $154 CA $172 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/f84b737e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Mobility Accessible](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/9c5d1ec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/ef9bad04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/8dbc27a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Little Lion [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) Great Barrington 8.6/10 Excellent (548 reviews) "Perfect for pets " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $153 CA $171 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/201806cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/77fe0507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/465e60d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/6761ce21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Mountain Lodge [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) Pittsfield 9.0/10 Wonderful (810 reviews) "Very comfortable and very close to ski slope and restaurants" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frederick CA $137 CA $184 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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=6005406&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Hinsdale Hotel Reviews ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Clean, very nice bed and linens, pool, jacuzzi, in room fireplace. Balcony right outside of living room. The breakfast was ok, they offered a lot but not top quality. The waffles were very good and the bacon. Overall excellent stay. Conveniently located to everything." [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Staff was very courteous and rooms clean." [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "The room and amenities were amazing. " [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Courtyard by Marriott Lenox Berkshires](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/b4c52f47_y.jpg) ### Courtyard by Marriott Lenox Berkshires 10/10 Excellent "Our stay was great! " [](https://expedia.ca/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "Perfectly Clean. Great Service. Beautiful Place!" [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Absolutely fabulous!" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "Wow. This hotel is such a great find. Not only is it clean and unique, the rooms are large and the staff are super helpful and nice. Breakfast was nice. The pool was slightly colder than I expected but it was 5 degrees outside and windy so its understandable. The hot tub was very comfortable. I would love to stay here again. My kids said this is their favorite hotel we have ever stayed at which is high praise since we travel frequently and have stayed in a ton of hotels!" [](https://expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Nice warm pool and hot tub. Good little fitness center. " [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "The rooms are clean, the pool is nice and the location is perfect for Jiminy Peak! " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Hinsdale? ### What is there to see and do in Hinsdale? ### When is the best time to book a hotel with a pool in Hinsdale? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Chalets in Becket ](https://www.expedia.ca/Becket-Chalets.d6005395-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Becket ](https://www.expedia.ca/Becket-Guest-Houses.d6005395-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Becket ](https://www.expedia.ca/Becket-Hotels-Cheap-Hotels.0-0-d6005395-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Becket ](https://www.expedia.ca/Becket-Hotels-Luxury-Hotel.0-0-d6005395-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Becket ](https://www.expedia.ca/Becket-Hotels-Mountain-Hotels.0-0-d6005395-tMountainHotels.Travel-Guide-Filter-Hotels) - 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