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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
2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in West Stockbridge
Pixley Forest | 15 Mins To Tanglewood • Fireplace
4 bedrooms, 6 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in West Stockbridge
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
10–15 Jul
5.0 out of 5 average rating, 17 reviews
Superhost
Room in West Stockbridge
Family Suite with a Balcony at Shaker Mill Inn
2 beds, 1 bathroom
21–26 Aug
Top guest favourite
Room in West Stockbridge
Standard Suite with a Patio at Shaker Mill Inn
3 beds, 1 bathroom
23–28 Jul
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in West Stockbridge
West Stockbridge MA gem, in town and facing lake
2 bedrooms, 2 queen beds, 2 bathrooms
23–29 Jul
4.95 out of 5 average rating, 40 reviews
Guest favourite
Home in West Stockbridge
Modern Log Cabin w/Pool & Views By Evergreen Home
4 bedrooms, 5 beds, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in West Stockbridge
Secluded Chic Mountain Chalet near Tanglewood
3 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
4.93 out of 5 average rating, 55 reviews
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed, 1 bathroom
17–22 Sept
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Barn in Town of Hillsdale
Blue Door Barn - Pond and Sweeping Views
1 bedroom, 2 beds, 1 bathroom
11–16 Jul
5.0 out of 5 average rating, 10 reviews
Guest favourite
Cottage in West Stockbridge
Historic 1810 Farmhouse - Fully Renovated
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.95 out of 5 average rating, 150 reviews
Guest favourite
Room in West Stockbridge
Standard Suite at Shaker Mill Inn
2 queen beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Cabin in Canaan
Newly Renovated Cabin in the Country
3 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.97 out of 5 average rating, 187 reviews
Top guest favourite
Cabin in Spencertown
Wake Up in the Woods, A Summer Reset Upstate
3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
4.96 out of 5 average rating, 25 reviews
Guest favourite
Home in West Stockbridge
Beautiful And Private Home Centrally Located
4 bedrooms, 7 beds, 3.5 bathrooms
21–26 Sept
4.97 out of 5 average rating, 62 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 197 reviews
Superhost
Room in West Stockbridge
Deluxe Suite with a Balcony Pets allowed
1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 6 reviews