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Search results; Over 1,000 places

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
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
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
46 min drive
Apr 20 – 25
5.0 out of 5 average rating, 319 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
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 Mount Washington
Beautiful Berkshires Colonial on 7 acres
10 min drive
May 3 – 8
5.0 out of 5 average rating, 30 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
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 Copake
Yellow Door House
26 min drive
Apr 21 – 26
4.92 out of 5 average rating, 38 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
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
Nature lodge in Sheffield
Sheffield Lodge - Ramblewood Master
32 min drive
Apr 27 – May 2
4.98 out of 5 average rating, 43 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
Home in Hillsdale
Modern Luxury Estate w/guesthouse, 45 scenic acres
21 min drive
Apr 20 – 25
New place to stay
Home in Sheffield
Bull Hill Bungalow
43 min drive
Apr 19 – 24
5.0 out of 5 average rating, 4 reviews
Superhost
Treehouse in New Marlborough
Double 3 Bedroom Tree House in the Berkshires
47 min drive
May 5 – 10
4.92 out of 5 average rating, 84 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
35 min drive
May 6 – 11
4.78 out of 5 average rating, 40 reviews
Guest favorite
Home in Sheffield
Race Mountain House
5 beds
Apr 21 – 26
4.85 out of 5 average rating, 114 reviews