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 - ![](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 prices for these dates Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2026-01-02&endDate=2026-01-04&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) ![Exterior](https://images.trvl-media.com/lodging/108000000/107090000/107080200/107080197/6b35157e.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) ### All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx. Lanesborough 10/10 Exceptional (45) "Weather didn't help but the rental and the location were exceptional!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) moe b. [](https://www.expedia.ca/Hancock-Hotels-All-Season-Adventures.h107080197.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) ![Lobby](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820158/caa9c80e.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) ![Pool](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820158/6110bb7d.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) ![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) ![Interior](https://images.trvl-media.com/lodging/96000000/95770000/95763800/95763744/90f12fde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants Hancock 9.0/10 Wonderful (12) "Great place to stay very clean and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick [](https://www.expedia.ca/Hancock-Hotels-In-The-HEART-Of-JIMINY-PEAK-MOUNTAIN-RESORT-Slope-Side.h95763744.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) ![Exterior](https://images.trvl-media.com/lodging/79000000/78440000/78431000/78430936/6a3ff8b6.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) ![Lobby](https://images.trvl-media.com/lodging/79000000/78440000/78431000/78430936/830491be.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 (18) "Perfect for a weekend of skiing with the family." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael D. [](https://www.expedia.ca/Hancock-Hotels-COZY-CABIN-IN-BERKSHIRES-RESORT-LABOR-DAY-SALE.h78430936.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) ![Pool](https://images.trvl-media.com/lodging/114000000/113830000/113820200/113820149/9f088c6b.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) ### 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) ![Lobby](https://images.trvl-media.com/lodging/107000000/106920000/106911300/106911243/3394ff12.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) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106920000/106911300/106911243/83905053.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) ### 1 Bd - Vacation Village in the Berkshires Hancock 10/10 Exceptional (2) "We enjoyed staying at this clean, quiet, and comfy property. Close to so many beautiful spots! Only minutes to both New York and Vermont!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin T. [](https://www.expedia.ca/Williamstown-Hotels-1-Bd-Vacation-Village-In-The-Berkshires.h106911243.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/37000000/36830000/36822800/36822714/6b3013ce.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) ![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) ![TV](https://images.trvl-media.com/lodging/102000000/101920000/101915200/101915147/f7a2fb55.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) ### 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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carrie C. [](https://www.expedia.ca/Hancock-Hotels-Bentley-Brook-Hancock.h101915147.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) ![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) ![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) "Fun time. Conditions were good. We love this family Mountain " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia H. [](https://www.expedia.ca/Hancock-Hotels-Bentley-Brook-Elevate-Your-Winter-Thrills-With-Premier-Ski-InSki-Out-Luxury.h101091040.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) ![TV](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916211/06cd6500.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) ### Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B Hancock [](https://www.expedia.ca/Hancock-Hotels-Bentley-Brook-Hancock.h101916211.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) ![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) ![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) "Jimney is always a great time" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zachary W. [](https://www.expedia.ca/Hancock-Hotels-Bentley-Brook-Ultimate-Ski-In-Ski-Out-Crazy.h101351994.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/102000000/101360000/101352400/101352326/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) ![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! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allison A. [](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) ![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) ![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) ### Pres Week- Bentley Brook Resort - Your Peak Winter Escape Hancock 9.6/10 Exceptional (4) "My family had a blast here and appreciate the availability. The property is situated perfectly for skiing on/off of Jiminy Cricket. Ski lockers made it even easier. We loved the spacious rooms, whirlpool bath, laundry and kitchen. My son said he wanted to move in :) Towels for bath and pool, coffee & filters, and laundry detergent provided. Free wifi and plenty of activities if you aren't skiing or apres-ski. There are 2 EV charging stations at one of the buildings and front desk avail 24/7. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy B. [](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/71000000/70600000/70595300/70595216/026f6fb2.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) ![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) ![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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) erica l. [](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/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) ![Game room](https://images.trvl-media.com/lodging/101000000/100900000/100899400/100899305/e7e0c62e.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) "Everything was great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alisa R. [](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/102000000/101090000/101081700/101081653/7c1792ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/102000000/101090000/101081700/101081653/78ca947a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/102000000/101090000/101081700/101081653/035c1041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/102000000/101090000/101081700/101081653/c4c29658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort Hancock [](https://www.expedia.ca/Hancock-Hotels-Unleash-Your-Alpine-Adventure-Wyndham-Bentley-Brook-Ski-In.h101081653.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) ![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) ![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) ### 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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eileen S. [](https://www.expedia.ca/Hancock-Hotels-Bentley-Brook-Hancock.h100402064.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) ![Lobby](https://images.trvl-media.com/lodging/102000000/101270000/101263700/101263676/ac56c0fa.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) ### Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury hancock 10/10 Exceptional (2) "The property manager was great and very communicative. The hotel is the perfect place to stay if skiing at Jiminy peak. Ski school right outside, pool and arcade room for the children." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danielle D. [](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) ![Pool](https://images.trvl-media.com/lodging/102000000/101270000/101264100/101264036/e38e6755.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) ### 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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edson S. [](https://www.expedia.ca/Hancock-Hotels-Embark-On-Alpine-Escapades-Bentley-Brook-Resort-Unveils-Ski-InSki-Out-Bliss.h101264036.Hotel-Information) ![Room](https://images.trvl-media.com/lodging/14000000/13240000/13232400/13232379/bbe606d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/14000000/13240000/13232400/13232379/f8ff0393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/14000000/13240000/13232400/13232379/3d8e78c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/14000000/13240000/13232400/13232379/6739e4f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Oak 'n Spruce Resort South Lee [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h13232379.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=2025-11-22&endDate=2025-11-23®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 ![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. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Hotel On North](//images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Perfect Stay in the Berkshire This hotel was spacious, clean, and had everything needed for a comfortable stay. The room was well-maintained, and the location was ideal—close to local attractions and easy to get around. Smooth check-in process and great access throughout. Highly recommend! " [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](//images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "I had a smooth check in. A little later I went back to the front desk to get an extra key, was asked my room number and last name. The associate, knew that I had asked for extra pillows when I made the reservation. I don't think he was even on my reservation on the computer yet to see the note. Asked if I had the extra pillows in the room and were they ok! Often hotels don't even notice this request, never mind remember it or ask about it. Great attention to details!" [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.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 "Everything was fine just no shampoo in the dispencer" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Great staff and the room was awesome!! Would definitely come again!" [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![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 "Spotless and friendly staff" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Clean, convenience, great staff, quiet, beautiful and secluded yet close to everything! Thank you" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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 "The amenities are great. The pool and hot tub are very comfortable temperatures, pool tables, ping pong, foosball, arcade games, movie theater, and more." [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ## Find out more about Berkshire County ## Berkshire County Resorts information | Number of reviews | 93 | | --- | --- | | Accommodation | 34 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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[Flights from Boston (BOS) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/bos/psf/boston-to-pittsfield) - [Flights from Ithaca (ITH) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/ith/psf/ithaca-to-pittsfield) - [Flights from Plattsburgh (PBG) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/pbg/psf/plattsburgh-to-pittsfield) - [Flights from Phoenix (PHX) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/phx/psf/phoenix-to-pittsfield) - [Flights from Richmond (RIC) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/ric/psf/richmond-to-pittsfield) - [Flights from Seattle (SEA) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/sea/psf/seattle-to-pittsfield) - [Flights from Toronto (YYZ) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/yyz/psf/toronto-to-pittsfield) - [Canoe Meadows Wildlife Sanctuary](https://www.expedia.ca/Canoe-Meadows-Wildlife-Sanctuary-Pittsfield.d553248621532665285.Vacation-Attraction) - [Hancock Shaker Village](https://www.expedia.ca/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction) - [Lenox Library](https://www.expedia.ca/Lenox-Library-Lenox.d553248621532665268.Vacation-Attraction) - [Ventfort Hall Mansion and Gilded Age Museum](https://www.expedia.ca/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Vacation-Attraction) - [Avis Rental Cars in Lenox](https://www.expedia.ca/Avis-Car-Rentals-In-Lenox.d8587-c41.Car-Rental-Guide-Suppliers) - [Budget Rental Cars in Pittsfield](https://www.expedia.ca/Budget-Car-Rentals-In-Pittsfield.d9478-c39.Car-Rental-Guide-Suppliers) - [Car rental Hancock](https://www.expedia.ca/Car-Rentals-In-Hancock.d112303.Car-Rental-Guide) - [Car rentals near Jiminy Peak Mountain Resort](https://www.expedia.ca/Car-Rentals-In-Jiminy-Peak-Mountain-Resort.d553248621532665536.Car-Rental-Guide) - [Car rental Lenox](https://www.expedia.ca/Car-Rentals-In-Lenox.d8587.Car-Rental-Guide) - [Rental cars Pittsfield Municipal airport](https://www.expedia.ca/Car-Rentals-In-Pittsfield-Municipal.d6031274.Car-Rental-Guide) - [Car rental Pittsfield](https://www.expedia.ca/Car-Rentals-In-Pittsfield.d9478.Car-Rental-Guide) - [Dalton Vacation Rentals](https://www.expedia.ca/Dalton-Vacation-Rentals.d6911.Travel-Guide-VacationRentals) - [Book Resorts in Berkshire County on Expedia.com](https://www.expedia.com/Berkshire-County-Resorts.d553248635083901436-aaResorts.Travel-Guide-Accommodation)