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Search resultsOver 1,000 places

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Includes all fees, before taxes
Home in New Marlborough
NEW Pet Friendly Berkshires Cottage Kayaks & Dock
3 min walk
Jun 26 – Jul 1
$200 per night
Home in New Marlborough
Lake House in the Berkshire (Dock access w/canoe
2 min walk
Jun 11 – 16
$290 per night
Superhost
Cottage in New Marlborough
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
1 min walk
Jul 8 – 15
$178 per night
Home in New Marlborough
Cozy home in the Berkshire woods
2 min walk
Sep 5 – 10
$259 per night
Home in Great Barrington
Amazing waterfront home with stone patio & kayaks!
1 min walk
Jun 10 – 17
$700 per night
Superhost
Home in New Marlborough
Cottage in the pines
1 min drive
Jun 19 – 26
$136 per night
Home in New Marlborough
Renovated Lakefront House w/ Dock: Pets Welcome!
1 min walk
Jun 12 – 17
$642 per night
Home in New Marlborough
Post and Beam Loft house, sleeps 9
13 min walk
Jul 6 – 11
$202 per night, originally $253
Superhost
Home in New Marlborough
Lake Buel Lakefront 4 Bedroom Cottage
1 min walk
Jun 24 – 29
$475 per night
Home in New Marlborough
Home base to explore the Berkshires
13 min walk
Jun 12 – 17
$190 per night
Superhost
Home in New Marlborough
Oak Hill House: A Berkshires escape with hot tub
4 min drive
Jun 11 – 16
$259 per night, originally $465
Superhost
Treehouse in New Marlborough
Double 3 Bedroom Tree House in the Berkshires
11 min drive
Jun 11 – 16
$199 per night
Superhost
Cottage in New Marlborough
Waterfront Lake Buel Cottage: 7 Mi to Monument Mtn
1 min walk
Aug 4 – 9
$286 per night
Cabin in Great Barrington
Modern Luxury Log Cabin Near Butternut Ski Area
3 min drive
Jun 11 – 16
$475 per night
Superhost
Guesthouse in Great Barrington
Barn Guesthouse w/ pool
7 min drive
Sep 19 – 25
$165 per night
Superhost
Home in Great Barrington
Light & bright modern tree house
4 min drive
Aug 26 – 31
$420 per night
Cabin in Monterey
Secluded cabin with babbling brook
9 min drive
Jul 30 – Aug 4
$200 per night
Home in Great Barrington
Lake House in the Heart of the Berkshires
2 min walk
Sep 6 – 11
$325 per night
Superhost