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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, 46 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, 31 reviews
Guest favourite
Cottage in West Stockbridge
Historic 1810 Farmhouse - Fully Renovated
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
4.95 out of 5 average rating, 152 reviews
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed, 1 bathroom
2–7 Aug
4.89 out of 5 average rating, 64 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.93 out of 5 average rating, 94 reviews
Top guest favourite
Flat in Lenox
Main Street Delight One Bedroom Apartment
1 bedroom, 1 queen bed, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 90 reviews
Top guest favourite
Place to stay in Canaan
Serene Berkshire Room with breakfast
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.94 out of 5 average rating, 104 reviews
Guest favourite
Home in West Stockbridge
Pixley Forest | 15 Mins To Tanglewood • Fireplace
4 bedrooms, 6 beds, 2 bathrooms
24–29 Aug
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Room in Great Barrington
Cozy & Convenient
1 queen bed, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Room in Great Barrington
Comfy single for a night or two (Eco Airbnb)
1 single bed, 1.5 bathrooms
1–6 Aug
4.93 out of 5 average rating, 54 reviews
Top guest favourite
Cabin in West Stockbridge
Cozy, two-bedroom cabin in a wooded glen
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 140 reviews
Guest favourite
Guest suite in Lenox
High Above Cliffwood (Full Apartment)
1 bedroom, 1 king bed, 1 bathroom
20–25 Aug
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Great Barrington
Cozy, Quiet Apt. in Housatonic, Great Barrington
1 bedroom, 2 beds, 2 bathrooms
4–9 Aug
5.0 out of 5 average rating, 38 reviews
Guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.84 out of 5 average rating, 154 reviews
Top guest favourite
Barn in Town of Hillsdale
Blue Door Barn - Pond and Sweeping Views
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
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
1–7 Jan
4.95 out of 5 average rating, 40 reviews
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed, 1 bathroom
12–17 Oct
4.98 out of 5 average rating, 50 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed, 2 bathrooms
13–18 Sept
4.93 out of 5 average rating, 346 reviews