Title: Browse the Best Berkshire County Resorts | Expedia.ca [Berkshire County Hotels](https://expedia.ca/Destinations-In-Berkshire-County.d553248635083901436.Hotel-Destinations)[Vacation Rentals in Berkshire County](https://expedia.ca/Destinations-In-Berkshire-County.d553248635083901436.Vacation-Rental-Destinations)[Berkshire County Car Rentals](https://expedia.ca/Destinations-In-Berkshire-County.d553248635083901436.Car-Rental-Destinations)[Berkshire County Vacations](https://expedia.ca/Berkshire-County.d553248635083901436.Destination-Travel-Guides) ![The Berkshires featuring snow as well as a family](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/71000/71827-The-Berkshires.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Resort Hotels in Berkshire County ## Compare and save ![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 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cities in Berkshire County ![Williamstown which includes café scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105596-Williamstown.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Williamstown [](https://expedia.ca/Williamstown-Resort-Hotels.d7859-aaResortHotels.Travel-Guide-Accommodation) ![Lenox featuring an administrative building](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105615-Lenox.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Lenox [](https://expedia.ca/Lenox-Resort-Hotels.d8587-aaResortHotels.Travel-Guide-Accommodation) ![North Adams featuring autumn colours](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105306-The-Berkshires.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### North Adams [](https://expedia.ca/North-Adams-Resort-Hotels.d9137-aaResortHotels.Travel-Guide-Accommodation) ![Great Barrington](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/238000/238015-Great-Barrington.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Great Barrington [](https://expedia.ca/Great-Barrington-Resort-Hotels.d110336-aaResortHotels.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/1/5c9675f1022a9d16db477be7ba7a1dae.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Stockbridge [](https://expedia.ca/Stockbridge-Resort-Hotels.d162575-aaResortHotels.Travel-Guide-Accommodation) ![Pittsfield showing a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105316-The-Berkshires.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Pittsfield [](https://expedia.ca/Pittsfield-Resort-Hotels.d9478-aaResortHotels.Travel-Guide-Accommodation) ## Featured Resorts in Berkshire County ![Lobby](https://images.trvl-media.com/lodging/108000000/107090000/107080200/107080197/96f0e35c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/108000000/107090000/107080200/107080197/02bfefec.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) ### 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) ![Interior](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820135/262c3ec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820135/47f32340.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) ### 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) ![Interior](https://images.trvl-media.com/lodging/96000000/95770000/95763800/95763744/90f12fde.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/96000000/95770000/95763800/95763744/63b60f05.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) ![Lobby](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820149/621d8f8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820149/b79738ca.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) ### 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) ![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/79000000/78440000/78431000/78430936/a5c5acbc.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) ![Interior](https://images.trvl-media.com/lodging/79000000/78440000/78431000/78430936/c5f7424d.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) ![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) ![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) ### 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) ![Interior](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820158/fe947738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820158/caa9c80e.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) ### 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) ![Pool](https://images.trvl-media.com/lodging/107000000/106920000/106911300/106911243/75d45394.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/102000000/101920000/101915200/101915147/b1cef878.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) ### 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) ![Exterior](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916211/529a2c1f.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) ![TV](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916211/06cd6500.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) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36830000/36822800/36822714/55af08d6.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) ![Interior](https://images.trvl-media.com/lodging/37000000/36830000/36822800/36822714/7d194d59.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/102000000/101360000/101352400/101352326/22d5f7a2.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) ### 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) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/102000000/101430000/101428500/101428437/a11cecf2.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/101000000/100900000/100899400/100899305/bef6f919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/101000000/100900000/100899400/100899305/e7e0c62e.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) ![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) ![Game room](https://images.trvl-media.com/lodging/71000000/70600000/70595300/70595216/b9ca1688.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) ![Game room](https://images.trvl-media.com/lodging/102000000/101100000/101091100/101091040/f8b384cf.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) ![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) ### 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) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100410000/100402100/100402064/e5d65058.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) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100410000/100402100/100402064/34c18366.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) ![Lobby](https://images.trvl-media.com/lodging/102000000/101360000/101352000/101351994/6d5af252.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) ### 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) ![Game room](https://images.trvl-media.com/lodging/102000000/101270000/101263700/101263676/a52152cd.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) ### 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) ![Game room](https://images.trvl-media.com/lodging/102000000/101270000/101264100/101264036/2ac3eeb4.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=2025-10-14&endDate=2025-10-15®ionId=553248635083901436&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%2FBerkshire-County-Resort-Hotels.d553248635083901436-aaResortHotels.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FBerkshire-County-Resort-Hotels.d553248635083901436-aaResortHotels.Travel-Guide-Accommodation) ## Top Berkshire County Hotel Reviews ![Hotel On North](//images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Absolutely loved every part of my stay at Hotel North. Parking was so easy and safe. The Hotel is decorated so tastefully, the staff was so welcoming. When I stepped into my room, I felt I had walked into a soothing refuge. Your decorators knew just how to balance the aesthetics with furnishings, art work, etc. Every detail was perfect - the room temperature, the comfortable bed, the quietness, etc. I will definitely recommend the Hotel North to anyone traveling to the Pittsfield area. Good job everyone!" [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](//images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Staff is friendly and accommodating " [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![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) ![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) ![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](//images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG 10/10 Excellent "Very nice hotel" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.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) ![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 "True to its historic character, the attention to detail was splendid! " [](https://expedia.ca/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 "Excellent hotel. Great staff. " [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ## Find out more about Berkshire County ## Berkshire County Resorts information | Number of reviews | 94 | | --- | --- | | Accommodation | 33 Resorts | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Aparthotels in Dalton](https://www.expedia.ca/Dalton-Apart-Hotels.d6911-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Dalton](https://www.expedia.ca/Dalton-Bed-And-Breakfast.d6911-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Dalton](https://www.expedia.ca/Dalton-Hotels-Cheap-Hotels.0-0-d6911-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Dalton](https://www.expedia.ca/Dalton-Hotels-Family-Hotel.0-0-d6911-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Dalton](https://www.expedia.ca/Dalton-Hotels-Spa-Hotel.0-0-d6911-tSpaHotel.Travel-Guide-Filter-Hotels) - 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