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The Berkshires vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in The Berkshires

Guests agree: these vacation rentals 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!
$73 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.
$208 per night
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Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
Hello hip, glamping cabin! The decor is chic & bohemian cool! Enjoy the large yard & sunny deck. Fieldstone fireplace w/ vaulted ceilings & skylights. Cottage has beautiful pine throughout w/ fabulous interior design picks. Enjoy the sweet reading nook, master bedroom w/ skylights or put on a favorite record. Kids will love the cozy sleeping loft. A 8-10 minute walk or 2 minute drive to lake public beach (The lovely Stockbridge Bowl) Outdoor shower. BBQ grill, great outdoor space to play.
$243 per night
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The Berkshires summer vacation rentals

Rental unit in Canaan
Mountain View Getaway
$100 per night
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Tiny home in Chatham
Sugar Shack - 300 square feet of pure sweetness.
$219 per night
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Cottage in Becket
Stylish Shales Brook Cottage-Cozy up to happiness
$218 per night
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Guesthouse in Stockbridge
Modern studio with views of the treetops
$138 per night
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Private room in Hillsdale
Sunny Victorian Suite by Catamount, Taconic Ridge
$97 per night
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Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
$167 per night
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Home in Lenox
Berkshire, MA Getaway! 1/2 mile to town!
$291 per night
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Cottage in Becket
BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.
$181 per night
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Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
$316 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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Cottage in Great Barrington
Cozy Country Cottage w Fireplace
$259 per night
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The Berkshires house rentals

Home in New Marlborough
Lake House in the Berkshire (Dock access w/canoe
$264 per night
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Home in Becket
Tranquil 3-BR Waterfront Retreat
$258 per night
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Home in Stockbridge
Bright Stockbridge country home, near everything!
$174 per night
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Private room in Lee
Warm & Welcoming Room w/ Private Bath
$104 per night
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Home in Becket
Woodland Haven in the Berkshires w/ Heated Pool
$451 per night
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Home in Cairo
Modern riverfront-swim just feet from your home
$280 per night
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Home in Great Barrington
Jaw dropping mountain & lake views
$695 per night
Home in Germantown
Scandinavian Upstate Barn with Catskill Views
$285 per night
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Home in Saugerties
The Hartwood House | Hot Tub, Hiking, Relax, Etc.
$341 per night
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Home in Kerhonkson
Architect's Hudson Valley Home in the Woods
$292 per night
Home in Egremont
Modern Farm House 5 minutes from Great Barrington
$299 per night
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Home in Richmond
LUXURY BERKSHIRES BARN! GRAND! VIEWS! 2/2
$185 per night
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The Berkshires condo rentals

Private room in Great Barrington
Quiet refuge in Great Barrington
$63 per night
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Condo in North Adams
Downtown Flat Iron Condo - walk to MoCA #14
$103 per night
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Condo in Lanesville
Trendy Condo on Hunter Mountain
$84 per night
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Condo in Lanesville
Stylish Condo on Hunter Mountain
$83 per night
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Condo in North Adams
Top Floor Downtown Studio - Walk to Mass MOCA!
$111 per night
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Condo in Hancock
Cozy Condo @Jiminy Peak
$163 per night
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Condo in Windham
Spring is for you , rest with us , cozy nest.
$90 per night
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Condo in Hancock
All-season Berkshires ski resort condo - Sitzmark
$206 per night
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Condo in Hancock
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4
$128 per night
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Condo in Hancock
Gorgeous Zen Must-See Suite At Jiminy Country Inn
$142 per night
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Condo in West Stockbridge
Modern & Comfy, 5★ Location ♛ 2BR Queen Bed ☀ Yard
$126 per night
Condo in Windham
Summer Retreat w/ Pool & Balcony
$72 per night