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Search results; Over 1,000 homes in Stockbridge

Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 bedrooms, 2 beds, 2.5 private bathrooms
13–18 Sept
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4.95 out of 5 average rating, 183 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 311 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.92 out of 5 average rating, 92 reviews
Top guest favourite
Cottage in Stockbridge
Quiet 2 BR cottage in the heart of the Berkshires
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.93 out of 5 average rating, 44 reviews
Guest favourite
Home in West Stockbridge
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Guest house in Stockbridge
Cottage with exquisite views
4 bedrooms, 5 beds, 4 bathrooms
1–6 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
4.99 out of 5 average rating, 92 reviews
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds, 3 bathrooms
9–14 Aug
5.0 out of 5 average rating, 36 reviews
Guest favourite
Home in Lee
Spacious Central Berkshires Home for Groups
4 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.91 out of 5 average rating, 46 reviews
Home in Stockbridge
Light-filled Carpenter's Cottage
1 bedroom, 1 bed, 1 bathroom
1–6 Aug
New place to stay
Guest favourite
Home in Stockbridge
Your Stockbridge Getaway
5 bedrooms, 8 beds, 2.5 bathrooms
23–28 Aug
4.96 out of 5 average rating, 26 reviews
Superhost
Flat in Great Barrington
King Bed|2m Ski Resort|Stylish|Fast Wi-Fi
1 king bed, 1 bathroom
19–24 Jul
4.88 out of 5 average rating, 83 reviews
Top guest favourite
Flat in Stockbridge
Three bedroom duplex in Stockbridge on the river
3 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
4.98 out of 5 average rating, 53 reviews
Flat in Pittsfield
Mid-Berkshires
2 bedrooms, 2 beds, 1 bathroom
22–27 Aug
New place to stay
Guest favourite
Guest suite in Lenox
High Above Cliffwood (Full Apartment)
1 bedroom, 1 king bed, 1 bathroom
31 Jul – 5 Aug
5.0 out of 5 average rating, 22 reviews
Home in Stockbridge
New England Family Retreat in Stockbridge, MA
4 bedrooms, 5 beds, 3 bathrooms
26–31 Jul
4.84 out of 5 average rating, 87 reviews
Top guest favourite
Cabin in Stockbridge
Lakeshore cabin with beach and dock
3 bedrooms, 5 beds, 2 bathrooms
3–8 Sept
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Home in Lenox
Home away from home: Minutes to Tanglewood.
3 bedrooms, 4 beds, 2.5 bathrooms
28 Sept – 3 Oct
4.94 out of 5 average rating, 51 reviews
Guest favourite
Home in Stockbridge
Stockbridge Cape Near Tanglewood!
4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.93 out of 5 average rating, 45 reviews