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Search results; Over 1,000 places

Boutique hotel in Lenox
Standard King in Boutique Lenox Hotel
1 king bed
Apr. 1 – 6
4.61 out of 5 average rating, 250 reviews
Guest favourite
Apartment in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
1 queen bed
Apr. 14 – 19
4.93 out of 5 average rating, 250 reviews
Guest favourite
Cottage in Becket
Cozy lakeside cottage
3 beds
Apr. 21 – 26
4.95 out of 5 average rating, 122 reviews
Superhost
Home in Becket
Real Estate:Therapy - Lake, Laundry, Love it
4 beds
Apr. 1 – 6
4.86 out of 5 average rating, 286 reviews
Guest favourite
Guesthouse in Lenox
Modern Barn with Loft at House on Golden Hill
3 beds
May 12 – 17
4.93 out of 5 average rating, 115 reviews
Guest favourite
Treehouse in Tyringham
Gingerbread House Tower in the Berkshire Hills
2 beds
Apr. 5 – 10
5.0 out of 5 average rating, 222 reviews
Guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bed
Apr. 1 – 6
4.99 out of 5 average rating, 101 reviews
Guest favourite
Guesthouse in Lenox
The Granary at House on Golden Hill
2 beds
Apr. 17 – 22
4.94 out of 5 average rating, 271 reviews
Guest favourite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
2 beds
Apr. 1 – 6
4.94 out of 5 average rating, 346 reviews
Superhost
Cabin in Stephentown
Cabin in the woods w cedar Hot Tub + private pond
2 queen beds
Apr. 1 – 6
4.84 out of 5 average rating, 232 reviews
Guest favourite
Barn in Great Barrington
Serene Renovated Barn w/ Firepit
2 beds
Apr. 1 – 6
5.0 out of 5 average rating, 45 reviews
Cabin in Monterey
Secluded cabin with babbling brook
3 beds
Apr. 8 – 13
4.86 out of 5 average rating, 195 reviews
Guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4 beds
Apr. 1 – 6
5.0 out of 5 average rating, 225 reviews
Guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
4 beds
Apr. 22 – 27
4.94 out of 5 average rating, 86 reviews
Guest favourite
Vacation home in Great Barrington
Home in Great Barrington. Steps from downtown!
3 beds
Jun. 2 – 7
4.94 out of 5 average rating, 131 reviews
Guest favourite
Tiny homes in Tyringham
Enchanted Tiny Tower nestled in the Berkshires
1 queen bed
Apr. 7 – 12
4.97 out of 5 average rating, 294 reviews
Guest favourite
Cottage in Great Barrington
Artist Cottage
1 queen bed
Apr. 29 – May 4
4.93 out of 5 average rating, 234 reviews
Superhost
Home in Becket
Lakeside 3-BR Berkshires Residence
3 queen beds
Apr. 1 – 6
New place to stay