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
Superhost
Apartment in Pittsfield
Cozy Chic - Studio Apartment
1 queen bed
Apr 2 – 7
New place to stay
Guest favorite
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 favorite
Cottage in Becket
Cozy lakeside cottage
3 beds
Apr 21 – 26
4.95 out of 5 average rating, 122 reviews
Guest favorite
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 favorite
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 favorite
Room in Great Barrington
Stay with Elaine
Quiet refuge in Great Barrington
Jun 8 – 13
4.96 out of 5 average rating, 148 reviews
Guest favorite
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
Guest suite in Lee
Cozy Guesthouse Near Downtown, Lee
2 queen beds
Apr 1 – 6
4.71 out of 5 average rating, 90 reviews
Cottage in New Lebanon
Carriage house suite in heart of the Berkshires
4 beds
Apr 1 – 6
4.62 out of 5 average rating, 253 reviews
Guest favorite
Treehouse in Tyringham
Gingerbread House Tower in the Berkshire Hills
2 beds
Apr 5 – 10
5.0 out of 5 average rating, 222 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 favorite
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 favorite
Guest suite in Great Barrington
Sweet 1-bedroom with salt water pool
1 queen bed
Apr 22 – 27
5.0 out of 5 average rating, 42 reviews
Guest favorite
Apartment in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 beds
Apr 1 – 6
4.83 out of 5 average rating, 153 reviews
Guest favorite
Cottage in Great Barrington
Artist Cottage
1 queen bed
Apr 29 – May 4
4.93 out of 5 average rating, 234 reviews
Guest favorite
Home in Stockbridge
Bright Stockbridge country home, near everything!
4 beds
Apr 22 – 27
4.94 out of 5 average rating, 86 reviews
Guest favorite
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