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Search results; Over 1,000 homes in Stockbridge

Descriptions are based on details hosts provide
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
Cabin in Stockbridge
Fieldstone fireplace and vaulted skylights near lake
4.89 out of 5 average rating, 246 reviews, 3 bedrooms, 5 beds, 1.5 bathrooms
9–14 Aug
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
Vaulted ceilings, hot tub, and private trails
4.97 out of 5 average rating, 62 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
21–26 Sept
Top guest favourite
Cottage in Stockbridge
Rustic woods cottage, 2 miles from Tanglewood
4.95 out of 5 average rating, 43 reviews, 2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
Guest favourite
Home in Lee
4BDR Elegant Berkshires Escape | Beaver Creek
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
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
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
4.97 out of 5 average rating, 91 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Stockbridge
Hand-built on 11 acres, mahogany decks
4.9 out of 5 average rating, 86 reviews, 4 bedrooms, 8 beds, 4 bathrooms
13–18 Sept
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4.99 out of 5 average rating, 311 reviews, 3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
Guest favourite
Home in Stockbridge
Rabbit Run in the heart of Stockbridge Village
4.89 out of 5 average rating, 123 reviews, 3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Flat in Stockbridge
Riverfront duplex in the Berkshire Mountains
4.98 out of 5 average rating, 53 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
Top guest favourite
Home in Lee
Split-level ranch near Tanglewood with fireplace
4.98 out of 5 average rating, 248 reviews, 3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
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
Home in Great Barrington
Historic home right on the Housatonic
4.46 out of 5 average rating, 26 reviews, 3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept
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
Top guest favourite
Cabin in Stockbridge
Lakeshore cabin with dock and kayaks
4.98 out of 5 average rating, 63 reviews, 3 bedrooms, 5 beds, 2 bathrooms
2–7 Sept
Top guest favourite
Home in Lenox
Stylish home with a fire pit
4.94 out of 5 average rating, 51 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
28 Sept – 3 Oct