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The best ski resorts in The Berkshires

Check out our pick of great ski resorts in The Berkshires

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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Situated within 10 km of Norman Rockwell Museum and 17 km of Tanglewood Musical Center, Granville House features rooms with air conditioning and a private bathroom in Great Barrington. With free private parking, the property is 18 km from Tanglewood and 19 km from Cranwell Spa & Golf Club. The bed and breakfast has family rooms. Cozy, cute property with very nice hosts. Parking is easy and free and check in was simple. The room was very comfortable and clean.

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9.8
Exceptional
135 reviews
Price from
US$269
per night

Set in Lee, 2.3 km from Cranwell Spa & Golf Club, Lakehouse Inn offers accommodation with a garden, free private parking, a terrace and a bar. 6.6 km from Tanglewood and 13 km from Norman Rockwell Museum, the inn features a range of water sports facilities. The property is non-smoking and is situated 6.4 km from Tanglewood Musical Center.

Guests at the accommodation will be able to enjoy activities in and around Lee, like hiking and skiing. Beautiful location, very clean and owner is a very honest guy that really cares

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9.4
Superb
150 reviews
Price from
US$172.37
per night

Situated in Pittsfield and within 13 km of Cranwell Spa & Golf Club, Hotel on North has a bar, non-smoking rooms, and free WiFi throughout the property. The property is around 13 km from Tanglewood Musical Center, 14 km from Tanglewood and 22 km from Norman Rockwell Museum. The accommodation features room service, an ATM and luggage storage for guests. Beautiful hotel with large, sunny, well-appointed rooms. Will definitely stay there again!

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9.1
Superb
188 reviews
Price from
US$169
per night

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires offers 3-star accommodation with an indoor pool, fitness centre and hot tub. Guests at the accommodation will be able to enjoy activities in and around Great Barrington, like hiking and skiing. Clean and comfortable. Very nice lobby

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9.2
Superb
104 reviews
Price from
US$159
per night

Located in Hancock just 35 miles from Norman Rockwell Museum, this hotel features an indoor and outdoor pool. Tennis courts and a hot tub are located on site. A full kitchen is featured in all suites. of having a snow rink at my bedroom door

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9
Superb
300 reviews
Price from
US$129
per night

Featuring an outdoor pool and mountain views, Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4 is located in Hancock. The air-conditioned accommodation is 33 km from Cranwell Spa & Golf Club. There is parking on-site and the property offers an electric vehicle charging station. My kids loved the games! It was perfect to take a break in a nice warm room and play some family games and have that quality time. The games ranged for little kids to teenagers which was perfect for us

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9
Superb
6 reviews
Price from
US$105
per night

2 Bed Berkshire Getaway minutes to Jiminy Peak Ski is situated in Hancock, 33 km from Tanglewood Musical Center, 33 km from Tanglewood, and 34 km from Cranwell Spa & Golf Club. The property is around 35 km from Rensselaer Polytechnic Institute, 37 km from Norman Rockwell Museum and 38 km from Albany-Rensselaer Amtrak. There is an outdoor fireplace and guests can make use of free WiFi and free private parking.

For guests with children, the apartment features outdoor play equipment. Guests at 2 Bed Berkshire Getaway minutes to Jiminy Peak Ski can enjoy skiing nearby, or make the most of the garden. Building is cute and easy to find. Parking was excellent being right in front of the door of this apartment. very clean, well stocked, modern space. Comfy living room for hanging out, large kitchen with everything you need to cook, a clean bathroom with soap, shampoo and toothbrushes and a big shower. It was cool I’m the house and easy to adjust the temperature. Location was good. Reasonably close to all the things we wanted to do, including Tanglewood, The Clark, Mass MoCA, the Mount, Lenox, Great Barrington, plus hiking, and skiing and horses next door! And a great cheese shop down the road (Four Fat Fowl).

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9.9
Exceptional
9 reviews
Price from
US$128.70
per night

Boasting air-conditioned accommodation with a private pool, Mountain View Suite on Jiminy Peak Ski On Off -New is situated in Hancock. The property has mountain views and is 33 km from Cranwell Spa & Golf Club and 33 km from Tanglewood Musical Center. The apartment offers parking on-site, an indoor pool and a lift. Beautiful area warm, comfortable room with a kitchen

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9
Superb
20 reviews
Price from
US$105
per night

Boasting air-conditioned accommodation with a patio, Downtown Great Barrington Enjoy Mountain Views is situated in Great Barrington. Both free WiFi and parking on-site are accessible at the holiday home free of charge. The property is non-smoking and is set 15 km from Norman Rockwell Museum. This house was extremely comfortable for us as a group and it was really nice to be able to cook and spend time together in a large open kitchen/dining space. The walk into town is easy, but the house and property feel like a private oasis. The hosts have paid a lot of attention to the detail of their home and we really appreciated their aesthetic as well as the practical components of their home. You can feel the thoughtful hospitality of the hosts even though they are not present, in the style and layout of their home.

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9.8
Exceptional
5 reviews
Price from
US$450
per night

For guests with children, the holiday home offers outdoor play equipment and a baby safety gate. Skiing, fishing and hiking are possible within the area, and Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak offers ski storage space. This was perfect for our family vacation reunion. There was plenty of space, both inside and outside. Lots of chairs and couches, outdoor seating, sports equipment, volley ball net, lots of green grass. The creak on the property was fun! We were able to enjoy the outdoor property facilities all morning, go on a trip in the afternoon-Jiminy Peak Mountain Adventure Park, 2 miles away, and one day we rented pontoons, on Lake Pontoosac, 20 minutes away. The nights we grilled supper and enjoyed a bonfire with the fire pit in the middle of the backyard. They even just added room air conditioners to the bedrooms, although the nights were cool and they weren't really necessary. 4 out of the 6 bedrooms have a bathroom attached, and there are 2 additional bathrooms on the main floor. Definitely met and exceeded all of our expectations!! Adults and children all had a grand time. I would highly recommend this property to anyone looking to vacation with extended family!

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9.4
Superb
9 reviews
Price from
US$397.63
per night

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