Search results; Over 1,000 homes

Top guest favorite
Cabin in East Nassau
Luxury Cabin | Fall Foliage, & Autumn Adventures
3 beds
Sep 21 – 26
ﺩ.ﺇ13,862 for 5 nights
5.0 out of 5 average rating, 54 reviews
Superhost
Home in Cheshire
Lakeside Oasis w/ Kayaks & Charm
2 beds
Aug 25 – 30
ﺩ.ﺇ7,965 for 5 nights
New place to stay
Guest favorite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
2 beds
Aug 31 – Sep 5
ﺩ.ﺇ6,940 for 5 nights
4.95 out of 5 average rating, 426 reviews
Top guest favorite
Home in Pittsfield
Cozy Cottage on Peaceful Pond, Close to Winery
2 beds
Sep 1 – 6
ﺩ.ﺇ7,637 for 5 nights
4.98 out of 5 average rating, 44 reviews
Guest favorite
Cottage in Becket
Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D
6 beds
Sep 14 – 19
ﺩ.ﺇ4,310 for 5 nights, originally ﺩ.ﺇ4,712
4.93 out of 5 average rating, 230 reviews
Guest favorite
Cottage in New Lebanon
The Writer's Cottage
2 beds
Aug 15 – 20
ﺩ.ﺇ2,433 for 5 nights
4.95 out of 5 average rating, 196 reviews
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Top guest favorite
Home in Lee
GreenHouse
2 beds
Nov 3 – 8
ﺩ.ﺇ3,875 for 5 nights
4.99 out of 5 average rating, 89 reviews
Superhost
Apartment in Great Barrington
King Bed|2mi Ski Resort|Fast Wi-Fi|Studio|
1 bed
Aug 17 – 22
ﺩ.ﺇ2,179 for 5 nights, originally ﺩ.ﺇ2,902
4.83 out of 5 average rating, 72 reviews
Top guest favorite
Cabin in Stockbridge
Stockbridge Snug- cabin luxury just steps to lake!
4 beds
Oct 12 – 17
ﺩ.ﺇ9,325 for 5 nights
4.97 out of 5 average rating, 31 reviews
Guest favorite
Home in Monterey
Jaw dropping mountain & lake views
4 beds
Sep 7 – 12
ﺩ.ﺇ14,207 for 5 nights
4.96 out of 5 average rating, 269 reviews
Guest favorite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
3 beds
Sep 7 – 12
ﺩ.ﺇ4,585 for 5 nights
4.92 out of 5 average rating, 97 reviews
Superhost
Home in Lee
Lakeside Getaway at Goose Pond!
5 beds
Sep 9 – 14
ﺩ.ﺇ6,419 for 5 nights, originally ﺩ.ﺇ7,229
Top guest favorite
Cabin in West Stockbridge
Cozy, two-bedroom cabin in a wooded glen
2 queen beds
Sep 28 – Oct 3
ﺩ.ﺇ5,799 for 5 nights
4.99 out of 5 average rating, 100 reviews
Guest favorite
Farm stay in New Lebanon
Barn Stay at Shadowbrook Farm
3 beds
Aug 30 – Sep 4
ﺩ.ﺇ5,425 for 5 nights
4.95 out of 5 average rating, 236 reviews
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 king beds
Sep 3 – 8
ﺩ.ﺇ4,456 for 5 nights
New place to stay
Top guest favorite
Home in Great Barrington
Granite Ledge, Modern home in a unique setting
3 beds
Sep 12 – 17
ﺩ.ﺇ8,563 for 5 nights, originally ﺩ.ﺇ9,283
4.99 out of 5 average rating, 126 reviews
Top guest favorite
Home in Great Barrington
Berkshires Black Abbey
4 beds
Sep 2 – 7
ﺩ.ﺇ12,041 for 5 nights
5.0 out of 5 average rating, 10 reviews
Superhost
Apartment in Great Barrington
Kitchenette|King Bed|Couch
1 bed
Aug 17 – 22
ﺩ.ﺇ2,605 for 5 nights, originally ﺩ.ﺇ3,204
4.88 out of 5 average rating, 119 reviews