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Search results; Over 1,000 places

Cabin in Plainfield
Camp on Windsor Pond- Berkshires
15 min drive
May 1 – 6
4.52 out of 5 average rating, 25 reviews
Home in Cummington
Massachusetts Vacation Rental w/ Deck & Grill
6 min drive
Apr 22 – 27
4.71 out of 5 average rating, 7 reviews
Cottage in Plainfield
Windsor Pond spacious get-away cottage
15 min drive
Jun 1 – 6
4.8 out of 5 average rating, 40 reviews
Guest favorite
Cabin in Savoy
The Camp - 20 Minutes to Berkshire East!
24 min drive
May 7 – 12
4.98 out of 5 average rating, 185 reviews
Superhost
Boutique hotel in Cummington
Singing Bridge Harmony Room
11 min drive
Apr 18 – 23
4.81 out of 5 average rating, 80 reviews
Boutique hotel in Lenox
Standard King in Boutique Lenox Hotel
53 min drive
Apr 18 – 23
4.62 out of 5 average rating, 261 reviews
Guest favorite
Cabin in Cummington
Just Be Cabin
24 min drive
Apr 21 – 26
4.98 out of 5 average rating, 161 reviews
Cabin in Plainfield
Peaceful Cabin in the Woods
23 min drive
Apr 21 – 26
4.91 out of 5 average rating, 106 reviews
Home in Cummington
River Forest House
11 min drive
May 1 – 6
4.82 out of 5 average rating, 55 reviews
Guest favorite
Apartment in Plainfield
Sunny carriage house apartment
23 min drive
May 1 – 6
4.95 out of 5 average rating, 237 reviews
Guest favorite
Apartment in Plainfield
Sunny, light filled loft in 1873 Colonial
22 min drive
Apr 18 – 23
4.97 out of 5 average rating, 238 reviews
Guest favorite
Home in Ashfield
An 18th century farmhouse
29 min drive
Apr 18 – 23
5.0 out of 5 average rating, 7 reviews
Guest favorite
Room in Cummington
Spacious private BR with king bed in Cummington!
20 min drive
Apr 18 – 23
4.92 out of 5 average rating, 26 reviews
Guest favorite
Cabin in North Adams
Mahican Cabin - A Private Nature's Reserve For 2
39 min drive
Apr 28 – May 3
4.95 out of 5 average rating, 182 reviews
Superhost
Cottage in Florida
Peaceful Mountain Cabin by Ski, Kayak, Museums +!
43 min drive
Apr 21 – 26
4.84 out of 5 average rating, 97 reviews
Superhost
Home in Cummington
Beautiful Secluded Country House
23 min drive
Apr 24 – 29
4.89 out of 5 average rating, 99 reviews
Guest favorite
Cabin in Hinsdale
Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere
34 min drive
Apr 24 – 29
4.9 out of 5 average rating, 70 reviews
Guest favorite
Chalet in Peru
Swiss Chalet Style Timberframe Home in Berkshires
33 min drive
Apr 20 – 25
4.92 out of 5 average rating, 249 reviews