Vacation rentals in Berkshire County

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Top-rated vacation rentals in Berkshire County

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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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