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Search results; Over 1,000 homes

Guest favorite
Apartment in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
20 min drive
May 5 – 10
4.93 out of 5 average rating, 255 reviews
Guest favorite
Cabin in Sheffield
House Cabin Vacation Rental in Berkshire County
6 queen beds
Apr 20 – 25
5.0 out of 5 average rating, 5 reviews
Guest favorite
Cottage in Copake Falls
Beautiful cottage at the foot of the Birkshires
16 min drive
Apr 19 – 24
4.91 out of 5 average rating, 317 reviews
Guest favorite
Home in Mount Washington
Beautiful Berkshires Colonial on 7 acres
10 min drive
May 3 – 8
5.0 out of 5 average rating, 30 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
32 min drive
May 19 – 24
4.81 out of 5 average rating, 248 reviews
Guest favorite
Home in Sheffield
Walt's Place-Your Family Getaway
5 beds
Apr 27 – May 2
4.98 out of 5 average rating, 44 reviews
Guest favorite
Cottage in Sheffield, The Berkshires
Cheerful 3-bedroom cottage with woodstove.
40 min drive
Apr 28 – May 3
4.93 out of 5 average rating, 102 reviews
Guest favorite
Home in Egremont
Modern Farm House 5 minutes from Great Barrington
25 min drive
Apr 19 – 24
4.93 out of 5 average rating, 256 reviews
Guest favorite
Home in Salisbury
Greystone at Twin Lakes
43 min drive
Apr 20 – 25
5.0 out of 5 average rating, 20 reviews
Guest favorite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
46 min drive
Apr 20 – 25
5.0 out of 5 average rating, 319 reviews
Cabin in Mount Washington
GORGEOUS BERKSHIRE/HUDSON VALLEY MOUNTAIN CABIN
10 min drive
Apr 21 – 26
5.0 out of 5 average rating, 5 reviews
Guest favorite
Home in Sheffield
House Among Trees - A Perfect Getaway
31 min drive
May 1 – 6
4.91 out of 5 average rating, 76 reviews
Guest favorite
Home in Sheffield
Private Berkshires Estate w/ Tennis Court
34 min drive
May 7 – 12
5.0 out of 5 average rating, 13 reviews
Guest favorite
Guest suite in Canaan
Walk to Brewery in Historic Railroad Depot
43 min drive
Apr 20 – 25
4.98 out of 5 average rating, 293 reviews
Guest favorite
Barn in Great Barrington
Serene Renovated Barn w/ Firepit
29 min drive
Apr 21 – 26
5.0 out of 5 average rating, 46 reviews
Guest favorite
Apartment in Sheffield
Private Berkshire Barn Apartment
36 min drive
Apr 23 – 28
4.92 out of 5 average rating, 121 reviews
Guest favorite
Chalet in Copake
Private upstate home nestled in the Hudson Valley
22 min drive
Apr 21 – 26
4.97 out of 5 average rating, 39 reviews
Guest favorite
Home in Copake
Yellow Door House
26 min drive
Apr 21 – 26
4.92 out of 5 average rating, 38 reviews