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Search results; Over 1,000 places

Guest favorite
Room in Dalton
Mother in Law unit in Dalton
7 min drive
Apr 1 – 6
4.96 out of 5 average rating, 137 reviews
Guest favorite
Home in Dalton
The Yellow House
8 min drive
Apr 15 – 20
4.91 out of 5 average rating, 112 reviews
Superhost
Apartment in Pittsfield
Cozy Chic - Studio Apartment
11 min drive
Apr 2 – 7
New place to stay
Guest favorite
Home in Pittsfield
Cantabile life in the Berkshires
7 min drive
Apr 7 – 12
4.94 out of 5 average rating, 98 reviews
Guest favorite
Cottage in Lanesborough
The Sail Loft
10 min drive
Apr 1 – 6
4.94 out of 5 average rating, 116 reviews
Superhost
Cottage in Lanesborough
Wildlife Lakeside Cottage
10 min drive
Apr 2 – 7
4.85 out of 5 average rating, 248 reviews
Guest favorite
Home in Pittsfield
Lake/Mountain View Getaway
12 min drive
Apr 2 – 7
4.98 out of 5 average rating, 41 reviews
Guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
19 min drive
Apr 1 – 6
4.99 out of 5 average rating, 101 reviews
Guest favorite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
11 min drive
Apr 7 – 12
4.99 out of 5 average rating, 374 reviews
Superhost
Home in Dalton
Willowbrook: A Sun Filled, Mid-century Modern Home
4 min drive
Apr 1 – 6
4.74 out of 5 average rating, 76 reviews
Apartment in Pittsfield
Renovated, Spacious, and Ideal for Families
9 min drive
Apr 1 – 6
New place to stay
Guest favorite
Home in Pittsfield
BB's Central Berkshire Home
11 min drive
Apr 1 – 6
4.96 out of 5 average rating, 48 reviews
Superhost
Home in Pittsfield
Central Berkshire Bungalow by Evergreen Home
11 min drive
Apr 1 – 6
4.9 out of 5 average rating, 30 reviews
Superhost
Home in Dalton
Brooksong, the perfect Berkshires getaway
12 min drive
Apr 2 – 7
4.92 out of 5 average rating, 169 reviews
Guest favorite
Apartment in Lanesborough
Cozy Berkshire Waterfront Home
16 min drive
Apr 1 – 6
5.0 out of 5 average rating, 21 reviews
Guest favorite
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
10 min drive
Apr 1 – 6
5.0 out of 5 average rating, 88 reviews
Guest favorite
Home in Lanesborough
Scenic mountain getaway.
18 min drive
Apr 9 – 14
5.0 out of 5 average rating, 46 reviews
Guest favorite
Home in Pittsfield
Family-Centric Berkshire Getaway by Evergreen Home
14 min drive
Apr 1 – 6
4.96 out of 5 average rating, 24 reviews