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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.

Private room in Sandisfield
Berkshire Hospitality and Comfort
Enjoy a rustic wooded retreat up in the cool Berkshire hills, surrounded by nature and wildlife, in a quiet, secluded, safe and peaceful setting, yet very close to top-notch cultural and recreational attractions. Nearby trails, pristine lakes and woods offer hiking, swimming and cycling. Experience the absence of mechanical sounds and the centering presence of rustling leaves, birdsong, and owls hooting at night. Behold a star-studded black night sky without artificial light. Breakfast included!
$70 per night
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Rental unit in Canaan
Mountain View Getaway
Come relax & enjoy panoramic mountain and pond views. Marvel at the dramatic lighting effects on Mercer Mt from sunrise-sunset from your private deck or bright & cheery living room. Fully equipped kitchen, bbq on the deck, short scenic drive to a wide variety of restaurants & endless cultural venues in the surrounding quaint villages of Berkshire County Mass and Columbia County NY. Near hiking trails, skiing, apple picking & farm stores. Queechy Lake swimming, NYS boat launch for car top boats.
$100 per night
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Cottage in Great Barrington
Romantic Cottage Get a way
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.
$229 per night
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Other great vacation rentals in Berkshire County

Guesthouse in Stockbridge
Modern studio with views of the treetops
$138 per night
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Rental unit in Great Barrington
Lush Setting, Private Deck, Queen Bed in GB
$109 per night
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Rental unit in Great Barrington
Private En Suite in Beautiful Victorian
$107 per night
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Private room in Dalton
Dalton in the Beautiful Berkshires
$73 per night
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Cabin in Canaan
Rustic Barn Studio Apartment
$145 per night
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Cottage in Great Barrington
Cozy Country Cottage w Fireplace
$242 per night
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Home in Lenox
Berkshire, MA Getaway! 1/2 mile to town!
$274 per night
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Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
$228 per night
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Cottage in Becket
BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.
$181 per night
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Rental unit in Sheffield
Hideaway with Spectacular Berkshire Views
$153 per night
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Cottage in New Lebanon
The Writer's Cottage
$115 per night
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Cottage in Becket
Stylish Shales Brook Cottage-Cozy up to happiness
$204 per night
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