Title: Browse the Best Cummington Resorts | Expedia.ca [Hotels in Cummington](https://expedia.ca/Cummington-Hotels.d183324.Travel-Guide-Hotels)[Vacation Rentals in Cummington](https://expedia.ca/Cummington-Vacation-Rentals.d183324.Travel-Guide-VacationRentals)[Cummington Car Rentals](https://expedia.ca/Car-Rentals-In-Cummington.d183324.Car-Rental-Guide)[Cummington Vacation Packages](https://expedia.ca/Cummington.d183324.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Resort Hotels in Cummington ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.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 Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=183324&startDate=2025-10-03&endDate=2025-10-05&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=183324&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183324&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=183324&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Cummington Resorts ![Lobby](https://images.trvl-media.com/lodging/108000000/107090000/107080200/107080197/96f0e35c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/108000000/107090000/107080200/107080197/13c36127.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107090000/107080200/107080197/6b35157e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/108000000/107090000/107080200/107080197/b9ce32d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx. Lanesborough 10/10 Exceptional (44) "Great place and location!" [](https://www.expedia.ca/Hancock-Hotels-All-Season-Adventures.h107080197.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820135/f0f0c14d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820135/a2eea2c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820135/2070c52d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820135/262c3ec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bentley Brook the perfect home base for exploring nearby Berkshire County Hancock 10/10 Exceptional (3) "We just spent a couple nights here but enjoyed our time here. There was plenty of room for 4 people and it was a close walk to the base of Jiminy Peak for the adventure park. Staff was helpful and friendly as well. " [](https://www.expedia.ca/Hancock-Hotels-Bentley-Brook-The-Perfect-Home-Base-For-Exploring-Nearby-Berkshire-County.h113820135.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/96000000/95770000/95763800/95763744/d5bc070a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/96000000/95770000/95763800/95763744/63b60f05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95770000/95763800/95763744/f5813f2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/96000000/95770000/95763800/95763744/47a328e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants Hancock 8.8/10 Excellent (11) "Great place to stay very clean and comfortable." [](https://www.expedia.ca/Hancock-Hotels-In-The-HEART-Of-JIMINY-PEAK-MOUNTAIN-RESORT-Slope-Side.h95763744.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820149/a6ce69c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820149/271a393e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820149/621d8f8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820149/9f088c6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bentley Brook the perfect home base for exploring nearby Berkshire County Hancock [](https://www.expedia.ca/Hancock-Hotels-Bentley-Brook-The-Perfect-Home-Base-For-Exploring-Nearby-Berkshire-County.h113820149.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/79000000/78440000/78431000/78430936/1ed8ac85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78440000/78431000/78430936/c5f7424d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/79000000/78440000/78431000/78430936/830491be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78440000/78431000/78430936/6a3ff8b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY. Hancock 9.6/10 Exceptional (17) "Perfect for a weekend of skiing with the family." [](https://www.expedia.ca/Hancock-Hotels-COZY-CABIN-IN-BERKSHIRES-RESORT-LABOR-DAY-SALE.h78430936.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107170000/107165100/107165016/07c04f3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107170000/107165100/107165016/ffffd558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107170000/107165100/107165016/1a00deb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/108000000/107170000/107165100/107165016/82887df2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more! Pittsfield 10/10 Exceptional (1) "We loved everything about this place! It was quiet, centrally located, and everyone was friendly and helpful. We will stay here again for sure!" [](https://www.expedia.ca/Pittsfield-Hotels-Charming-1-Bedroom-4-Star-Resort-W-Heated-Pool.h107165016.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820158/dbb7cb70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820158/6110bb7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820158/83866e1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820158/fe947738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bentley Brook the perfect home base for exploring nearby Berkshire County Hancock 10/10 Exceptional (1) [](https://www.expedia.ca/Hancock-Hotels-Bentley-Brook-The-Perfect-Home-Base-For-Exploring-Nearby-Berkshire-County.h113820158.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/107000000/106920000/106911300/106911243/3394ff12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106920000/106911300/106911243/515247d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/107000000/106920000/106911300/106911243/59bd216a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106920000/106911300/106911243/83905053.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1 Bd - Vacation Village in the Berkshires Hancock 10/10 Exceptional (2) "Great spot" [](https://www.expedia.ca/Williamstown-Hotels-1-Bd-Vacation-Village-In-The-Berkshires.h106911243.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101920000/101915200/101915147/796d7f85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101920000/101915200/101915147/b0805b20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/102000000/101920000/101915200/101915147/f7a2fb55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/102000000/101920000/101915200/101915147/2d7b79dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A Hancock 10/10 Exceptional (1) "We really enjoyed our stay and it was nice to be so close to the slopes." [](https://www.expedia.ca/Hancock-Hotels-Bentley-Brook-Hancock.h101915147.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916211/1c4aecd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916211/481cb70f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916211/529a2c1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916211/8b24fbaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B Hancock [](https://www.expedia.ca/Hancock-Hotels-Bentley-Brook-Hancock.h101916211.Hotel-Information) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/37000000/36830000/36822800/36822714/a45d128d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36830000/36822800/36822714/6b3013ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/37000000/36830000/36822800/36822714/0e9154fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36830000/36822800/36822714/55af08d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Village In The Berkshires 5 Star Resort - Suite B Hancock [](https://www.expedia.ca/Hancock-Hotels-Vacation-Village-In-The-Berkshires-5-Star-Resort-Suite-B.h36822714.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/102000000/101360000/101352400/101352326/c04c2f29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games, table tennis](https://images.trvl-media.com/lodging/102000000/101360000/101352400/101352326/w1298h837x1y2-b03a6bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/102000000/101360000/101352400/101352326/ea6a1087.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/102000000/101360000/101352400/101352326/5b082fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out Hancock 10/10 Exceptional (6) "Great location, clean and perfect for a family! " [](https://www.expedia.ca/Hancock-Hotels-Bentley-Brook-Alpine-Haven-Premier-Ski-InSki-Out.h101352326.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/102000000/101430000/101428500/101428437/9728288b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/102000000/101430000/101428500/101428437/09614d74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/102000000/101430000/101428500/101428437/91d3fa3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/102000000/101430000/101428500/101428437/14bfab23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pres Week- Bentley Brook Resort - Your Peak Winter Escape Hancock 9.6/10 Exceptional (4) "Bentley Brook is the ideal location for a young family on a ski trip!" [](https://www.expedia.ca/Hancock-Hotels-Frost-Peaks-Bentley-Brook-Resort-Your-Peak-Winter-Escape.h101428437.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/101000000/100900000/100899400/100899305/1c158c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/101000000/100900000/100899400/100899305/bef6f919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/101000000/100900000/100899400/100899305/fba7de3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/101000000/100900000/100899400/100899305/c7a73a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base Hancock 10/10 Exceptional (3) "This property is great for skiing, especially with kids. There is a nice pool and little movie theater thats prefect for after a day on the slopes." [](https://www.expedia.ca/Hancock-Hotels-Bentley-Brook-Resort-Premier-Retreat-At-Jiminy-Peaks-Base.h100899305.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/71000000/70600000/70595300/70595216/026f6fb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/71000000/70600000/70595300/70595216/b9ca1688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/71000000/70600000/70595300/70595216/2143f660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/71000000/70600000/70595300/70595216/9bd50e6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hot SKI-in SKI-out Rentals Bentley Brook Resort! Hancock 10/10 Exceptional (1) "Great property! Great location. Smooth check-in." [](https://www.expedia.ca/Hancock-Hotels-Hot-SKI-In-SKI-Out-Rentals-Bentley-Brook-Resort.h70595216.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/102000000/101100000/101091100/101091040/73547cfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games, DVD player, table tennis](https://images.trvl-media.com/lodging/102000000/101100000/101091100/101091040/w1298h837x1y2-cbed74c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/102000000/101100000/101091100/101091040/36a55cc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/102000000/101100000/101091100/101091040/80af228a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jiminy Premier Ski-In/Ski-Out Resort Bentley B Hancock 10/10 Exceptional (2) "Great place to get my 6 year old on the mountain. What a great time !" [](https://www.expedia.ca/Hancock-Hotels-Bentley-Brook-Elevate-Your-Winter-Thrills-With-Premier-Ski-InSki-Out-Luxury.h101091040.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/101000000/100410000/100402100/100402064/ae96910c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/101000000/100410000/100402100/100402064/3d493137.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100410000/100402100/100402064/e5d65058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/101000000/100410000/100402100/100402064/de459953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl Hancock 10/10 Exceptional (1) "Large property with ski-in/ski-out proximity to Jiminy Peak. Units are standard but large, clean, and with helpful amenities for a family vacation (kitchenette in unit, plus nice pool for kids' apres-ski, kids' movies, etc.) We'll be back." [](https://www.expedia.ca/Hancock-Hotels-Bentley-Brook-Hancock.h100402064.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/102000000/101360000/101352000/101351994/ee95ee05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/102000000/101360000/101352000/101351994/4a2cabfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/102000000/101360000/101352000/101351994/be0edbc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/102000000/101360000/101352000/101351994/8bd1d979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bentley Brook: Ultimate Ski-In Ski-Out -Crazy Hancock 9.6/10 Exceptional (4) "Very easy access to the slope and perfect for family with kids" [](https://www.expedia.ca/Hancock-Hotels-Bentley-Brook-Ultimate-Ski-In-Ski-Out-Crazy.h101351994.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/102000000/101270000/101263700/101263676/57a9a4fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/102000000/101270000/101263700/101263676/ca14f101.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/102000000/101270000/101263700/101263676/4a1b23ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/102000000/101270000/101263700/101263676/ac56c0fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury hancock 10/10 Exceptional (2) "This condo was perfect for our family. We had lots of space and we were right on the base of Jiminy peak. I would definitely stay again." [](https://www.expedia.ca/Hancock-Hotels-Ski-InSki-Out-Bliss-Bentley-Brook-Resort-SlopeSideLuxury.h101263676.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/102000000/101270000/101264100/101264036/d8011dea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/102000000/101270000/101264100/101264036/c5e59f98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/102000000/101270000/101264100/101264036/68708401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/102000000/101270000/101264100/101264036/e38e6755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss Hancock 10/10 Exceptional (1) "Walked out of the building, straight into my kids skiing lessons, very convenient." [](https://www.expedia.ca/Hancock-Hotels-Embark-On-Alpine-Escapades-Bentley-Brook-Resort-Unveils-Ski-InSki-Out-Bliss.h101264036.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=2025-10-10&endDate=2025-10-11®ionId=183324&adults=2&lodging=HOTEL_RESORT&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FCummington-Resort-Hotels.d183324-aaResortHotels.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCummington-Resort-Hotels.d183324-aaResortHotels.Travel-Guide-Accommodation) ## Top Cummington Hotel Reviews ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again. " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Comfort Inn & Suites](//images.trvl-media.com/lodging/1000000/560000/558100/558078/d1319a54_y.jpg) ### Comfort Inn & Suites 10/10 Excellent "Very clean, very quiet, very close to UMass " [](https://expedia.ca/Springfield-Hotels-Comfort-Inn-Suites.h558078.Hotel-Information) ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "What a beautiful place. I wish I could have stayed longer. Top notch!" [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.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 "It's just a nice place and the staff is very nice " [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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 "Clean, spacious, well designed room with everything needed gir a great stay …. And so much more. The balcony was a great place to sit, gave coffee etc. can’t say enough about the beautiful grounds and amenities like indoor and outdoor pool areas, etc! Enjoyed staying at Vacation Village in the Berkshire and hope to return next time I am in the area. " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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 "The restaurant was very good" [](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Inn on Boltwood](//images.trvl-media.com/lodging/3000000/2030000/2027100/2027065/f10073da_y.jpg) ### Inn on Boltwood 10/10 Excellent "Great stay" [](https://expedia.ca/Springfield-Hotels-Inn-On-Boltwood.h2027065.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.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![The Ellery](//images.trvl-media.com/lodging/1000000/900000/892700/892654/0b76727c_y.jpg) ### The Ellery 10/10 Excellent "Enjoyed our stay, convenient to a number of leisure activities. Clean and comfortable, would stay here again. " [](https://expedia.ca/Springfield-Hotels-The-Ellery.h892654.Hotel-Information) ## Find out more about Cummington ## Cummington Resorts information | Number of reviews | 94 | | --- | --- | | Accommodation | 30 Resorts | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [B&B in Ashfield](https://www.expedia.ca/Ashfield-Bed-And-Breakfast.d3000421239-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Ashfield](https://www.expedia.ca/Ashfield-Hotels-Cheap-Hotels.0-0-d3000421239-tCheapHotels.Travel-Guide-Filter-Hotels) - [Ashfield Hotels](https://www.expedia.ca/Ashfield-Hotels.d3000421239.Travel-Guide-Hotels) - [Apartments in Chesterfield](https://www.expedia.ca/Chesterfield-Apartments.d89029-aaApartments.Travel-Guide-Accommodation) - [B&B in Chesterfield](https://www.expedia.ca/Chesterfield-Bed-And-Breakfast.d89029-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Chesterfield](https://www.expedia.ca/Chesterfield-Cabins.d89029-aaCabins.Travel-Guide-Accommodation) - 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