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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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4.9 out of 5 average rating, 157 reviews
Top guest favourite
Cottage in Stockbridge
Quiet 2 BR cottage in the heart of the Berkshires
2 bedrooms, 3 beds
24–29 Aug
4.95 out of 5 average rating, 43 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 310 reviews
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 bedrooms, 2 queen beds
31 Aug – 5 Sept
4.96 out of 5 average rating, 181 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 90 reviews
Guest favourite
Home in Lee
Spacious Central Berkshires Home for Groups
4 bedrooms, 3 queen beds
7–12 Sept
4.91 out of 5 average rating, 44 reviews
Guest favourite
Home in Stockbridge
New England Family Retreat in Stockbridge, MA
4 bedrooms, 5 beds
19–24 Jul
4.85 out of 5 average rating, 86 reviews
Top guest favourite
Flat in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
1 bedroom, 1 queen bed
5–10 Sept
4.96 out of 5 average rating, 122 reviews
Superhost
Home in Stockbridge
Mac Shores | 5 min to Tanglewood ! • Shared Beach
3 bedrooms, 4 beds
29 Jul – 3 Aug
4.81 out of 5 average rating, 16 reviews
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed
18–23 Sept
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
27 Aug – 1 Sept
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Lee
Stylish Berkshires Retreat
2 bedrooms, 2 queen beds
19–24 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Lee
Berkshire 4 season home
3 bedrooms, 3 queen beds
25–30 Oct
4.98 out of 5 average rating, 248 reviews
Guest favourite
Flat in Lee
Beautiful Berkshires 1-BR Apartment
1 bedroom, 1 double bed
19–24 Jul
4.95 out of 5 average rating, 19 reviews
Superhost
Flat in Great Barrington
King Bed|2m Ski Resort|Stylish|Fast Wi-Fi
1 king bed
12–17 Jul
4.88 out of 5 average rating, 80 reviews
Guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
1 bedroom, 1 bed
23–28 Aug
4.85 out of 5 average rating, 151 reviews
Superhost
Home in Stockbridge
Moss's Muse: A Modern Retreat
4 bedrooms, 4 beds
25–30 Jul
New place to stay
Top guest favourite
Cabin in Stockbridge
Lakeshore cabin with beach and dock
3 bedrooms, 5 beds
2–7 Sept
4.98 out of 5 average rating, 63 reviews
Guest favourite
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
3 bedrooms, 5 beds
9–14 Aug
4.89 out of 5 average rating, 246 reviews