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Search results; Over 1,000 homes in West Stockbridge

Chalet in West Stockbridge
Modern Mtn Chalet | Great Barrington & Tanglewood
3 bedrooms, 10 beds, 2.5 private bathrooms
31 Aug – 5 Sept
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4.96 out of 5 average rating, 45 reviews
Top guest favourite
Guest house in West Stockbridge
Guest House 15 mins to Tanglewood
5.0 out of 5 average rating, 26 reviews, 2 beds, 1 bathroom
7–12 Sept
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Home in West Stockbridge
Pixley Forest | 15 Mins To Tanglewood • Fireplace
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 6 beds, 2 bathrooms
24–29 Aug
Guest favourite
Home in West Stockbridge
Modern Log Cabin w/Pool & Views By Evergreen Home
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
13–18 Sept
Guest favourite
Home in West Stockbridge
Exceptional Stockbridge Retreat
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
10–15 Jul
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Home in West Stockbridge
West Stockbridge MA gem, in town and facing lake
4.95 out of 5 average rating, 40 reviews, 2 bedrooms, 2 beds, 2 bathrooms
23–29 Jul
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Home in West Stockbridge
Secluded Chic Mountain Chalet near Tanglewood
4.93 out of 5 average rating, 55 reviews, 3 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
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Room in West Stockbridge
Standard Suite with a Patio at Shaker Mill Inn
5.0 out of 5 average rating, 11 reviews, 3 beds, 1 bathroom
23–28 Jul
Guest favourite
Cottage in West Stockbridge
Historic 1810 Farmhouse - Fully Renovated
4.95 out of 5 average rating, 150 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Superhost
Room in West Stockbridge
Family Suite with a Balcony at Shaker Mill Inn
2 beds, 1 bathroom
21–26 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
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4.99 out of 5 average rating, 309 reviews, 3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
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Cabin in Spencertown
Wake Up in the Woods, A Summer Reset Upstate
4.96 out of 5 average rating, 25 reviews, 3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
4.95 out of 5 average rating, 166 reviews, 3 bedrooms, 4 beds, 1 bathroom
12–17 Jul
Top guest favourite
Cottage in Great Barrington
Artist Cottage
4.93 out of 5 average rating, 342 reviews, 1 bedroom, 1 bed, 2 bathrooms
7–12 Sept
Guest favourite
Room in West Stockbridge
Standard Suite at Shaker Mill Inn
5.0 out of 5 average rating, 7 reviews, 2 queen beds, 1 bathroom
19–24 Jul
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
4.99 out of 5 average rating, 311 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Top guest favourite
Home in West Stockbridge
Berkshires-Enjoy The Peak, private home
4.94 out of 5 average rating, 104 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Sept