Search results; Over 1,000 places

Guest favorite
Place to stay in Stockbridge
Cozy room w/private bath–near Kripalu/ Tanglewood
10 min drive
Sep 6 – 11
R12,431 ZAR for 5 nights
4.86 out of 5 average rating, 92 reviews
Guest favorite
Guesthouse in Stockbridge
Light-filled Carpenter's Cottage in Stockbridge
10 min drive
Sep 7 – 12
R16,490 ZAR for 5 nights
4.94 out of 5 average rating, 33 reviews
Guesthouse in West Stockbridge
Guest House 15 mins from Tanglewood
20 min drive
Jul 28 – Aug 2
R13,425 ZAR for 5 nights
New place to stay
Top guest favorite
Home in Stockbridge
Secluded Family Home in Serene Stockbridge Woods
12 min walk
Sep 1 – 6
R43,233 ZAR for 5 nights, originally R47,315 ZAR
4.98 out of 5 average rating, 55 reviews
Home in West Stockbridge
Exceptional Stockbridge Retreat
10 min drive
Jul 9 – 14
R39,111 ZAR for 5 nights
Room in Stockbridge
Iris Room bright with 4 windows :)
5 min walk
Jan 4 – 9
R15,856 ZAR for 5 nights
4.26 out of 5 average rating, 38 reviews
Top guest favorite
Apartment in Stockbridge
Stockbridge private apartment
10 min drive
Sep 8 – 13
R23,255 ZAR for 5 nights
4.98 out of 5 average rating, 54 reviews
Guest favorite
Guesthouse in Stockbridge
Modern barn in the heart of the Berkshires
2 queen beds
Jul 20 – 25
R21,289 ZAR for 5 nights, originally R24,277 ZAR
4.92 out of 5 average rating, 131 reviews
Guest favorite
Cottage in Great Barrington
The Cottage at The Barrington House
10 min drive
Aug 3 – 8
R20,084 ZAR for 5 nights, originally R23,997 ZAR
4.94 out of 5 average rating, 137 reviews
Guest favorite
Apartment in Great Barrington
King Bed | Patio | 2m to Ski Resort
20 min drive
Jul 13 – 18
R9,197 ZAR for 5 nights, originally R20,313 ZAR
4.91 out of 5 average rating, 92 reviews
Guest favorite
Apartment in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
20 min drive
Jul 13 – 18
R9,197 ZAR for 5 nights, originally R20,313 ZAR
4.93 out of 5 average rating, 89 reviews
Guest favorite
Room in Great Barrington
Quiet refuge in Great Barrington
20 min drive
Jul 13 – 18
R7,717 ZAR for 5 nights, originally R8,873 ZAR
4.95 out of 5 average rating, 189 reviews
Guest favorite
Guesthouse in Stockbridge
Modern studio with views of the treetops
10 min drive
Sep 7 – 12
R18,076 ZAR for 5 nights
4.95 out of 5 average rating, 235 reviews
Top guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
30 min drive
Aug 3 – 8
R14,651 ZAR for 5 nights, originally R18,653 ZAR
4.99 out of 5 average rating, 229 reviews
Top guest favorite
Room in Lee
Warm & Welcoming Room w/ Private Bath
20 min drive
Aug 3 – 8
R11,099 ZAR for 5 nights
4.98 out of 5 average rating, 215 reviews
Home in West Stockbridge
Peaceful spacious home, secluded woodland property
10 min drive
Jul 20 – 25
R49,195 ZAR for 5 nights
Guest favorite
Room in Lee
Beautiful Downtown Lee setting
20 min drive
Jul 9 – 14
R12,727 ZAR for 5 nights
4.85 out of 5 average rating, 493 reviews
Home in Lee
Laurel House
20 min drive
Jul 13 – 18
R42,361 ZAR for 5 nights
5.0 out of 5 average rating, 3 reviews