Search results; Over 1,000 places

Guest favorite
Room in Great Barrington
Quiet refuge in Great Barrington
20 min drive
Jul 6 – 11
R7,833 ZAR for 5 nights, originally R9,607 ZAR
for 5 nights
4.95 out of 5 average rating, 187 reviews
Superhost
Room in Great Barrington
Comfy single for a night or two (Eco Airbnb)
20 min drive
Jul 5 – 10
R7,095 ZAR for 5 nights
for 5 nights
4.85 out of 5 average rating, 27 reviews
Guest favorite
Home in Monterey
Charming cottage w/ gorgeous views.
20 min drive
Jul 6 – 11
R17,978 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 336 reviews
Top guest favorite
Apartment in Great Barrington
Private En Suite in Beautiful Victorian
20 min drive
Sep 7 – 12
R11,236 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 371 reviews
Top guest favorite
Cottage in Monterey
Beaver Lodge
10 min drive
Aug 24 – 29
R24,334 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 60 reviews
Superhost
Apartment in Great Barrington
Writer's retreat: study, books, fireplace (Ecobnb)
20 min drive
Jul 8 – 13
R15,954 ZAR for 5 nights
for 5 nights
4.78 out of 5 average rating, 18 reviews
Top guest favorite
Home in New Marlborough
Cottage in the heart of Mill River Village
20 min drive
Jul 1 – 6
R23,414 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 9 reviews
Top guest favorite
Home in Monterey
Berkshires Retreat | Fenced Yard + Near Tanglewood
10 min drive
Jul 1 – 6
R70,155 ZAR for 5 nights, originally R83,050 ZAR
for 5 nights
5.0 out of 5 average rating, 21 reviews
Top guest favorite
Loft in Great Barrington
The Old Red Barn
20 min drive
Jul 14 – 19
R19,797 ZAR for 5 nights
for 5 nights
4.99 out of 5 average rating, 332 reviews
Top guest favorite
Apartment in Sheffield
Private Berkshire Barn Apartment
30 min drive
Jul 8 – 13
R13,869 ZAR for 5 nights, originally R16,570 ZAR
for 5 nights
4.93 out of 5 average rating, 151 reviews
Guest favorite
Apartment in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
20 min drive
Jul 6 – 11
R18,320 ZAR for 5 nights, originally R27,593 ZAR
for 5 nights
4.88 out of 5 average rating, 84 reviews
Guest favorite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
10 min drive
Jul 30 – Aug 4
R27,480 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 88 reviews
Top guest favorite
Home in Great Barrington
Prime location for the best of the Berkshires
10 min drive
Aug 26 – 31
R26,603 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 114 reviews
Top guest favorite
Guesthouse in Sheffield
Black Bear Bungalow, Sheffield Mass. U Will Love!
30 min drive
Jul 20 – 25
R18,299 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 16 reviews
Top guest favorite
Cottage in Monterey
New! Fully renovated private cottage
10 min drive
Jul 9 – 14
R34,158 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 25 reviews
Guest favorite
Apartment in Great Barrington
Kitchenette|King Bed|Couch
20 min drive
Jul 27 – Aug 1
R25,575 ZAR for 5 nights, originally R32,508 ZAR
for 5 nights
4.89 out of 5 average rating, 105 reviews
Top guest favorite
Home in Lee
Berkshire 4 season home
30 min drive
Nov 1 – 6
R22,836 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 215 reviews
Guest favorite
Room in Great Barrington
Large, light bedroom on The Hill (Eco Airbnb)
20 min drive
Jul 14 – 19
R8,832 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 7 reviews