Title: Book the Best Hotels with POOL in Western Massachusetts in 2025 | Expedia.ca [Western Massachusetts Travel Guide](https://expedia.ca/Western-Massachusetts.dx6234063)[Hotels in Western Massachusetts](https://expedia.ca/Western-Massachusetts-Hotels.d6234063.Travel-Guide-Hotels)[Vacation Rentals in Western Massachusetts](https://expedia.ca/Western-Massachusetts-Vacation-Rentals.d6234063.Travel-Guide-VacationRentals)[Flights to Western Massachusetts](https://expedia.ca/Cheap-Flights-To-Western-Massachusetts.d6234063.Travel-Guide-Flights)[Western Massachusetts Car Rentals](https://expedia.ca/Car-Rentals-In-Western-Massachusetts.d6234063.Car-Rental-Guide)[Western Massachusetts Vacation Packages](https://expedia.ca/Western-Massachusetts.d6234063.Destination-Travel-Guides) ![A panorama of western Massachusetts from the top of Mount Greylock](https://images.trvl-media.com/place/6234063/25d665be-4bef-4d30-84bb-d5865c866e81.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Western Massachusetts, MA - ![](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 Western Massachusetts Hotels with a Pool Tonight [Nov 13 - Nov 14](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2025-11-13&endDate=2025-11-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 14 - Nov 15](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2025-11-14&endDate=2025-11-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Western Massachusetts Hotels with a Pool ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/62ab3ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/11bb9318.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG Great Barrington 8.8/10 Excellent (692) "Solid location, great room, good breakfast. Fair Price. Been 3 different times and look forward to returning again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jamie CA $143 CA $160 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.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/a25612d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (954) "Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacey CA $124 CA $138 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f43c89bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3a8723ec.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/f3c92221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/4ea5ab50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham Lenox 9.2/10 Wonderful (1000) "Great place. Friendly staff and very well located. Great breakfast options. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abiezer CA $140 CA $156 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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) ![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) ![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) ### Vacation Village in the Berkshires Williamstown 8.8/10 Excellent (2134) "We came here because it was off season, great price, and it had an indoor pool. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Monica CA $127 CA $157 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Indoor pool, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/a0205904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/f36d24b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/08190a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/2bcbba21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru by Hilton Chicopee Springfield Chicopee 8.8/10 Excellent (1000) " Staff was wonderful and hotel was spotless. Great breakfast also!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Theresa CA $122 CA $139 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.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) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/f1aeba62.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 9.6/10 Exceptional (10) "Very friendly with dog. No complaints with accommodations " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lilian CA $189 CA $211 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/5c3a2624.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/bd8e0182.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/8c645106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/eaa5d51b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott West Springfield West Springfield 9.2/10 Wonderful (563) "The hotel is wonderful and located close to shopping and some nice local restaurants. The staff was very attentive and thoughtful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $166 CA $189 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/35e3e6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/w3838h2587x1y0-b516eca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Refrigerator](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/04ad8e9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/w3839h2584x0y3-17f28d6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Westfield Westfield 8.4/10 Very good (808) "Good staff, clean, convenient" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Harlan CA $149 CA $167 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-By-Hilton-Westfield.h2076197.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/662f1ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 Bedroom Condo 1/2 mile from base | In-room dining](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/40940c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/a8f10f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/ddfadf2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jiminy Peak Mountain Resort Hancock 8.2/10 Very good (984) "We didn't spend much time there, but it was nice, comfortable, clean and quiet. It was close to the things we had planned to do." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Philip CA $202 CA $226 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/28000000/27670000/27664900/27664860/1442e379.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/28000000/27670000/27664900/27664860/4a2b5204.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![8 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/28000000/27670000/27664900/27664860/c76c1f43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bars/lounges](https://images.trvl-media.com/lodging/28000000/27670000/27664900/27664860/ce9b3f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MGM Springfield Metro Center 9.0/10 Wonderful (1429) "Room and staff were great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $189 CA $247 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Springfield-Hotels-MGM-Springfield.h27664860.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=2025-11-27&endDate=2025-11-28®ionId=6234063&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Western Massachusetts Hotel Reviews ![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 "The staff were awesome! Both ladies at the front desk were so nice and accommodating. Would definitely stay there again!" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Springfield MA](//images.trvl-media.com/lodging/1000000/20000/18100/18056/71c77a60_y.jpg) ### La Quinta Inn & Suites by Wyndham Springfield MA 10/10 Excellent "Had a great time " [](https://expedia.ca/Springfield-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Springfield-MA.h18056.Hotel-Information) ![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 "Good " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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 "Staff…great Room…great We enjoy it here and stay annually " [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Red Roof Inn PLUS+ South Deerfield – Amherst](//images.trvl-media.com/lodging/1000000/790000/789000/788985/20ee398b_y.jpg) ### Red Roof Inn PLUS+ South Deerfield – Amherst 10/10 Excellent "Helpful and friendly staff. Rooms comfortable " [](https://expedia.ca/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information) ![Hilton Garden Inn-Springfield, MA](//images.trvl-media.com/lodging/1000000/900000/892100/892040/2726a1b6_y.jpg) ### Hilton Garden Inn-Springfield, MA 10/10 Excellent "Everything was wonderful from the friendly staff to the extremely comfortable and clean room. The reason we chose the hotel was due to location and the pool. The pool and amenities did not disappoint." [](https://expedia.ca/Springfield-Hotels-Hilton-Garden-Inn-Springfield.h892040.Hotel-Information) ![D. Hotel Suites & Spa](//images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg) ### D. Hotel Suites & Spa 10/10 Excellent "Very comfortable stay" [](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "The staff was amazing, so kind and accommodating. The room was clean, the beds were very comfortable. Nice breakfast options. We were in town for a concert at Mahaiwe and we didn’t use our car once we checked in… a great home base for the weekend. Will definitely be back. " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.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 "I love the ambience - historic and comfortable and excellent food. 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