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Search results; Over 1,000 places

Guest favorite
Cottage in Great Barrington
Cottage on Scenic Road
1 queen bed
Apr 26 – May 1
4.91 out of 5 average rating, 224 reviews
Guest favorite
Farm stay in New Lebanon
Barn Stay at Shadowbrook Farm
3 beds
Apr 21 – 26
4.95 out of 5 average rating, 184 reviews
Guest favorite
Home in Lenox
Heart of Lenox Walk to Town Cozy Cottage!
3 beds
May 9 – 14
4.93 out of 5 average rating, 207 reviews
Guest favorite
Cottage in Sheffield, The Berkshires
Cheerful 3-bedroom cottage with woodstove.
5 beds
Apr 28 – May 3
4.93 out of 5 average rating, 102 reviews
Guest favorite
Apartment in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
1 bed
May 5 – 10
5.0 out of 5 average rating, 15 reviews
Guest favorite
Cottage in Copake Falls
Beautiful cottage at the foot of the Birkshires
2 queen beds
Apr 20 – 25
4.91 out of 5 average rating, 317 reviews
Guest favorite
Room in Pittsfield
Stay with JosieDigital production,
Large guest suite w/private bath in the Berkshires
Apr 20 – 25
4.99 out of 5 average rating, 374 reviews
Guest favorite
Apartment in Pittsfield
Luxury 2BR Apt. Home w/Work Area
2 beds
Apr 26 – May 1
4.96 out of 5 average rating, 52 reviews
Superhost
Cottage in Becket
Private Lake Cottage on 3 acres w/350 sq. ft. deck
4 beds
Apr 20 – 25
4.76 out of 5 average rating, 139 reviews
Guest favorite
Cottage in Bethlehem
Cottage Getaway | Peaceful Setting | Pet Friendly
2 beds
Apr 21 – 26
5.0 out of 5 average rating, 31 reviews
Superhost
Cabin in Stephentown
Cabin in the woods w cedar Hot Tub + private pond
2 queen beds
Apr 25 – 30
4.84 out of 5 average rating, 236 reviews
Guest favorite
Apartment in Great Barrington
Walk Everywhere! | Relax in Easy Elegance!
3 beds
Apr 26 – May 1
5.0 out of 5 average rating, 92 reviews
Guest favorite
Home in Becket
Berkshires Retreat W/ Sauna by Evergreen Home
7 beds
Apr 21 – 26
4.96 out of 5 average rating, 49 reviews
Guest favorite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
2 beds
Apr 20 – 25
5.0 out of 5 average rating, 319 reviews
Guest favorite
Cottage in West Stockbridge
Historic 1810 Farmhouse - Fully Renovated
4 beds
Apr 22 – 27
4.98 out of 5 average rating, 106 reviews
Superhost
Home in Becket
Real Estate:Therapy - Lake, Laundry, Love it
4 beds
Apr 28 – May 3
4.86 out of 5 average rating, 287 reviews
Guest favorite
Guesthouse in Pittsfield
The Nest at Birdland
4 beds
Apr 20 – 25
4.98 out of 5 average rating, 47 reviews
Guest favorite
Cabin in West Stockbridge
Modern Cabin near Tanglewood
5 beds
Apr 23 – 28
4.98 out of 5 average rating, 46 reviews