Search results; Over 1,000 homes in Stockbridge

Guest favorite
Place to stay in Stockbridge
Cozy room w/private bath–near Kripalu/ Tanglewood
1 bed
Sep 4 – 9
ﺩ.ﺇ2,540 for 5 nights
4.85 out of 5 average rating, 99 reviews
Top guest favorite
Apartment in Stockbridge
Stockbridge private apartment
2 beds
Sep 8 – 13
ﺩ.ﺇ4,736 for 5 nights
4.98 out of 5 average rating, 60 reviews
Guesthouse in West Stockbridge
Guest House near hiking trails and excellent cafes
2 beds
Sep 9 – 14
ﺩ.ﺇ2,734 for 5 nights
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Stockbridge
Cozy, welcoming Berkshires cabin – come unplug!
2 beds
Aug 11 – 16
ﺩ.ﺇ4,111 for 5 nights, originally ﺩ.ﺇ5,463
5.0 out of 5 average rating, 3 reviews
Guesthouse in Stockbridge
Cottage with exquisite views
5 beds
Sep 2 – 7
ﺩ.ﺇ11,551 for 5 nights
5.0 out of 5 average rating, 3 reviews
Guest favorite
Apartment in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
1 queen bed
Sep 1 – 6
ﺩ.ﺇ5,812 for 5 nights
4.96 out of 5 average rating, 111 reviews
Top guest favorite
Cabin in Stockbridge
Stockbridge Snug- cabin luxury just steps to lake!
4 beds
Oct 12 – 17
ﺩ.ﺇ9,437 for 5 nights
4.97 out of 5 average rating, 31 reviews
Guest favorite
Cottage in Great Barrington
The Cottage at The Barrington House
1 queen bed
Sep 7 – 12
ﺩ.ﺇ3,466 for 5 nights
4.94 out of 5 average rating, 143 reviews
Apartment in Stockbridge
Historic Retreat
1 queen bed
Aug 10 – 15
ﺩ.ﺇ5,575 for 5 nights
4.87 out of 5 average rating, 52 reviews
Guest favorite
Guesthouse in Stockbridge
Modern studio with views of the treetops
2 beds
Sep 7 – 12
ﺩ.ﺇ3,681 for 5 nights
4.95 out of 5 average rating, 239 reviews
Guest favorite
Guesthouse in Stockbridge
Light-filled Carpenter's Cottage in Stockbridge
1 queen bed
Aug 17 – 22
ﺩ.ﺇ4,693 for 5 nights
4.94 out of 5 average rating, 35 reviews
Guest favorite
Guesthouse in Lenox
The Coach House | Modern 2BR Loft + Views & Pool
3 beds
Nov 3 – 8
ﺩ.ﺇ2,381 for 5 nights, originally ﺩ.ﺇ4,851
4.9 out of 5 average rating, 261 reviews
Guest favorite
Cottage in Stockbridge
Quiet 2 BR cottage in the heart of the Berkshires
3 beds
Sep 2 – 7
ﺩ.ﺇ6,824 for 5 nights
4.95 out of 5 average rating, 37 reviews
Guest favorite
Guesthouse in Lenox
Restored 1735 Granary I King Bed + Views & Pool
2 beds
Oct 28 – Nov 2
ﺩ.ﺇ3,123 for 5 nights, originally ﺩ.ﺇ3,720
4.93 out of 5 average rating, 390 reviews
Top guest favorite
Room in Lee
Stay with AndreaWeb designer,
Warm & Welcoming Room w/ Private Bath
Sep 15 – 20
ﺩ.ﺇ2,368 for 5 nights
4.98 out of 5 average rating, 221 reviews
Superhost
Home in Stockbridge
Summer Cottage at The Lake!
4 beds
Sep 10 – 15
ﺩ.ﺇ6,133 for 5 nights, originally ﺩ.ﺇ8,142
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Home in Stockbridge
Charming Stockbridge Farmhouse- walk to town!
6 beds
Aug 9 – 14
ﺩ.ﺇ9,407 for 5 nights, originally ﺩ.ﺇ11,261
5.0 out of 5 average rating, 14 reviews
Apartment in Stockbridge
One bedroom in Charming Berkshires Farmhouse
1 bed
Aug 13 – 18
ﺩ.ﺇ4,365 for 5 nights
5.0 out of 5 average rating, 3 reviews