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Vacation rentals in Berkshire County

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Top-rated vacation rentals in Berkshire County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Cabin in Stephentown
Cabin in the woods w cedar Hot Tub + private pond
The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.
$229 per night
Cottage in Great Barrington
Artist Cottage
Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.
$179 per night
Guest suite in Williamstown
Berkshire Guest Suite
Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.
$85 per night

Other great vacation rentals in Berkshire County

Guesthouse in Lenox
The Granary at House on Golden Hill
$97 per night
Apartment in Sheffield
Private Berkshire Barn Apartment
$105 per night
Treehouse in Tyringham
Gingerbread House Tower in the Berkshire Hills
$235 per night
Guesthouse in Stockbridge
Modern studio with views of the treetops
$157 per night
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
$299 per night
Apartment in Great Barrington
Private En Suite in Beautiful Victorian
$107 per night
Home in Chester
Riverfront Getaway
$149 per night
Home in Lenox
Berkshire, MA Getaway! Mile to town
$191 per night
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
$150 per night
Cabin in Canaan
Rustic Barn Studio Apartment
$145 per night
Home in New Lebanon
The old sawmill from 1771
$125 per night
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
$318 per night

Destinations to explore