Search cottages in The Berkshires

Featuring a hot tub, Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak is set in Hancock. Boasting private check-in and check-out, this property also provides guests with an outdoor fireplace. There is a sun terrace and guests can make use of free WiFi and free private parking. 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!

Situated 2.5 km from Tanglewood Musical Center, 2.7 km from Tanglewood and 11 km from Norman Rockwell Museum, Walk to Dining Downtown Lenox Guest House! features accommodation located in Lenox. The property is set 41 km from Great Falls, 42 km from Canaan Village Historic District and 44 km from The Clark Art Institute. Free WiFi is available throughout the property and Cranwell Spa & Golf Club is 2.4 km away. Very quiet, decent size. Good kitchen equipments, good location, private parking, we did enjoy the stay.

The Mill River Cabin with Fireplace and River View! is situated in Mill River, 35 km from Cranwell Spa & Golf Club, 35 km from Tanglewood Musical Center, as well as 35 km from Tanglewood. The property is around 13 km from Great Falls, 13 km from Canaan Village Historic District and 20 km from Haystack Mountain State Park. Free WiFi is available throughout the property and Norman Rockwell Museum is 30 km away. the cabin is wonderful in a beautiful setting, overlooking a stream. it was cozy and warm, with everything we needed to enjoy our stay. we were able to cook and dine in comfort, and warm ourselves with the wood burning stove.

Situated 47 km from Cranwell Spa & Golf Club, Clover Hill Farm & Country Inn provides accommodation in Williamstown with access to a hot tub. The property has mountain and inner courtyard views, and is 25 km from Bennington Battle Monument. The farm stay features rooms with air conditioning, free private parking and free WiFi. super friendly. super close to the university. Best owners - got a bluberry pie on my way back to Boston ;-).

The spacious holiday home is fitted with 3 bedrooms, a TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. Towels and bed linen are featured in the holiday home. The accommodation offers a fireplace. The amenities, the area, the appliances, the games and coziness of this house are 10/10. If you are looking for a place to have fun with your friends/family then this is 100% the place you should book. Also it is worth mentioning that the host is incredibly responsive and an amazing host.

The spacious holiday home comes with 2 bedrooms, a TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. The accommodation offers a fireplace.

Located in Hancock, 33 km from Tanglewood Musical Center and 33 km from Tanglewood, The entire Stephentown Hotel. 28 person occupancy offers air conditioning. The property is around 34 km from Cranwell Spa & Golf Club, 35 km from Rensselaer Polytechnic Institute and 37 km from Norman Rockwell Museum. There is an outdoor fireplace and guests can make use of free WiFi and free private parking.

Situated in Sheffield, 28 km from Cranwell Spa & Golf Club and 28 km from Tanglewood Musical Center, 4 Mi to Great Barrington Berkshires Retreat! offers air conditioning. The property is around 28 km from Tanglewood, 16 km from Great Falls and 16 km from Canaan Village Historic District. Free WiFi is available throughout the property and Norman Rockwell Museum is 21 km away.

The spacious holiday home has 4 bedrooms, a TV, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 3 bathrooms with a bath. Towels and bed linen are available in the holiday home. The accommodation offers a fireplace.

Featuring air-conditioned accommodation with a private pool, Bougie Bs Mountainside Getaway is set in Hancock. It is located 33 km from Cranwell Spa & Golf Club and offers a 24-hour front desk. Offering free WiFi throughout the property, the non-smoking holiday home has a hot tub.