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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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4.91 out of 5 average rating, 159 reviews
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
4.96 out of 5 average rating, 182 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
8–13 Sept
Guest favourite
Home in Stockbridge
Your Stockbridge Getaway
4.96 out of 5 average rating, 26 reviews, 5 bedrooms, 8 beds, 2.5 bathrooms
23–28 Aug
Guest favourite
Home in West Stockbridge
Beautiful And Private Home Centrally Located
4.97 out of 5 average rating, 62 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
21–26 Sept
Top guest favourite
Guest house in Stockbridge
Cottage with exquisite views
5.0 out of 5 average rating, 21 reviews, 4 bedrooms, 5 beds, 4 bathrooms
1–6 Sept
Top guest favourite
Cottage in Stockbridge
Quiet 2 BR cottage in the heart of the Berkshires
4.95 out of 5 average rating, 43 reviews, 2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
Top guest favourite
Home in Stockbridge
Just a min from Downtown Stockbridge on 11 Acres
4.9 out of 5 average rating, 86 reviews, 4 bedrooms, 8 beds, 4 bathrooms
13–18 Sept
Guest favourite
Home in Stockbridge
New England Family Retreat in Stockbridge, MA
4.84 out of 5 average rating, 87 reviews, 4 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
4.97 out of 5 average rating, 90 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4.99 out of 5 average rating, 310 reviews, 3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
Top guest favourite
Home in Lenox
Home away from home: Minutes to Tanglewood.
4.94 out of 5 average rating, 51 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
28 Sept – 3 Oct
Guest favourite
Home in Stockbridge
Greek Revival Farmhouse
4.97 out of 5 average rating, 128 reviews, 3 bedrooms, 5 beds, 2 bathrooms
21–28 Aug
Superhost
Home in Stockbridge
Mac Shores | 5 min to Tanglewood ! • Shared Beach
4.81 out of 5 average rating, 16 reviews, 3 bedrooms, 4 beds, 1 bathroom
29 Jul – 3 Aug
Home in Stockbridge
Light Filled - Modern Rustic Home
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
Top guest favourite
Cabin in Stockbridge
Lakeshore cabin with beach and dock
4.98 out of 5 average rating, 63 reviews, 3 bedrooms, 5 beds, 2 bathrooms
2–7 Sept
Guest favourite
Home in Stockbridge
Rabbit Run in the heart of Stockbridge Village
4.89 out of 5 average rating, 122 reviews, 3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Guest favourite
Home in West Stockbridge
Exceptional Stockbridge Retreat
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Aug
Home in Great Barrington
Cozy Riverside Retreat in the Berkshires
4.46 out of 5 average rating, 26 reviews, 3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Lee
Berkshire 4 season home
4.98 out of 5 average rating, 248 reviews, 3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct