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Search results; Over 1,000 homes in West Stockbridge

Guest favourite
Cottage in West Stockbridge
Historic 1810 Farmhouse - Fully Renovated
3 bedrooms, 4 beds, 2 private bathrooms
19–24 Jul
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4.95 out of 5 average rating, 150 reviews
Top guest favourite
Guest house in West Stockbridge
Guest House 15 mins to Tanglewood
5.0 out of 5 average rating, 29 reviews, 2 beds, 1 bathroom
7–12 Sept
Guest favourite
Home in West Stockbridge
8 Mi to Tanglewood & Butternut Ski: Spacious Home!
4.87 out of 5 average rating, 23 reviews, 6 bedrooms, 7 beds, 3.5 bathrooms
1–6 Sept
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
Guest favourite
Home in West Stockbridge
Pixley Forest | 15 Mins To Tanglewood • Fireplace
5.0 out of 5 average rating, 14 reviews, 4 bedrooms, 6 beds, 2 bathrooms
24–29 Aug
Top guest favourite
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
Top guest favourite
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
Superhost
Room in West Stockbridge
Deluxe Suite with a Balcony Pets allowed
5.0 out of 5 average rating, 6 reviews, 1 queen bed, 1 bathroom
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
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
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
4.98 out of 5 average rating, 44 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Sept
Top guest favourite
Barn in Town of Hillsdale
Blue Door Barn - Pond and Sweeping Views
5.0 out of 5 average rating, 11 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Jul – 4 Aug
Top guest favourite
Cottage in Great Barrington
Artist Cottage
4.93 out of 5 average rating, 343 reviews, 1 bedroom, 1 bed, 2 bathrooms
7–12 Sept
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
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
4.95 out of 5 average rating, 168 reviews, 3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept
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
Superhost
Room in West Stockbridge
Suite with a Patio at Shaker Mill Inn Pets allowed
4.75 out of 5 average rating, 4 reviews, 3 beds, 1 bathroom
20–25 Jul
Superhost
Room in West Stockbridge
Family Suite with a Balcony at Shaker Mill Inn
2 beds, 1 bathroom
21–26 Aug
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