Search results; Over 1,000 homes in Stockbridge

Guest favourite
Guest house in Stockbridge
Modern barn in the heart of the Berkshires
2 bedrooms, 2 beds, 1 private bathroom
30 Aug – 4 Sept
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4.91 out of 5 average rating, 159 reviews
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 queen beds
8–13 Sept
4.96 out of 5 average rating, 182 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4 beds
20–25 Sept
4.99 out of 5 average rating, 311 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
2 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 91 reviews
Guest favourite
Home in Stockbridge
Stockbridge Cape Near Tanglewood!
5 beds
27 Jul – 1 Aug
4.93 out of 5 average rating, 45 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 queen bed
7–12 Sept
4.93 out of 5 average rating, 343 reviews
Top guest favourite
Cottage in Stockbridge
Quiet 2 BR cottage in the heart of the Berkshires
3 beds
24–29 Aug
4.95 out of 5 average rating, 43 reviews
Top guest favourite
Guest house in Stockbridge
Cottage with exquisite views
5 beds
1–6 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Lee
GreenHouse
2 beds
24–29 Oct
4.99 out of 5 average rating, 132 reviews
Guest favourite
Home in Lee
Spacious Central Berkshires Home for Groups
3 queen beds
7–12 Sept
4.91 out of 5 average rating, 45 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
4 beds
23–28 Aug
4.83 out of 5 average rating, 6 reviews
Guest favourite
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
5 beds
9–14 Aug
4.89 out of 5 average rating, 246 reviews
Top guest favourite
Home in Lee
Berkshire 4 season home
3 queen beds
25–30 Oct
4.98 out of 5 average rating, 248 reviews
Top guest favourite
Flat in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
1 queen bed
5–10 Sept
4.96 out of 5 average rating, 122 reviews
Guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
1 bed
23–28 Aug
4.84 out of 5 average rating, 152 reviews
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
4 beds
9–14 Aug
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 beds
2–7 Aug
4.99 out of 5 average rating, 92 reviews
Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
4 beds
25–30 Aug
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 beds
27 Aug – 1 Sept
5.0 out of 5 average rating, 26 reviews