Search results; Over 1,000 homes

Guest favorite
Home in Great Barrington
Lovely house in the Berkshires
4 min walk
Aug 25 – 30
R27,794 ZAR for 5 nights
5.0 out of 5 average rating, 6 reviews
Superhost
Home in New Marlborough
Lake House in the Berkshire (Access Dock & Canoe
2 min walk
Aug 31 – Sep 5
R38,138 ZAR for 5 nights
4.88 out of 5 average rating, 139 reviews
Superhost
Cottage in New Marlborough
Pet friendly Cottage on Lake; Hike, Swim, Kayak
3 min walk
Sep 7 – 12
R35,003 ZAR for 5 nights
4.91 out of 5 average rating, 43 reviews
Superhost
Home in Great Barrington
Fall Weekends: Waterfront, Dock, Kayaks!
1 min walk
Sep 21 – 26
R58,513 ZAR for 5 nights
4.96 out of 5 average rating, 26 reviews
Guest favorite
Home in New Marlborough
Modern Lake Home in the Berkshire Woods
2 min walk
Sep 2 – 7
R35,630 ZAR for 5 nights
4.91 out of 5 average rating, 97 reviews
Home in New Marlborough
Renovated Lakefront House w/ Dock: Pets Welcome!
1 min walk
Aug 23 – 28
R60,853 ZAR for 5 nights
4.6 out of 5 average rating, 15 reviews
Home in Great Barrington
Design-forward Berkshires cabin
10 min drive
Aug 29 – Sep 3
R52,444 ZAR for 5 nights, originally R62,595 ZAR
New place to stay
Guest favorite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
10 min drive
Sep 7 – 12
R22,256 ZAR for 5 nights
4.92 out of 5 average rating, 97 reviews
Home in New Marlborough
Rustic Cabin in the forest of Lake Buel
4 min walk
Aug 15 – 20
R15,673 ZAR for 5 nights
4.47 out of 5 average rating, 17 reviews
Home in Great Barrington
Lake Buel Retreat: Stunning Views and Private Dock
1 min walk
Aug 18 – 23
R64,782 ZAR for 5 nights
4.63 out of 5 average rating, 38 reviews
Top guest favorite
Home in Great Barrington
Prime location for the best of the Berkshires
10 min drive
Sep 7 – 12
R24,032 ZAR for 5 nights
4.97 out of 5 average rating, 117 reviews
Top guest favorite
Cabin in Great Barrington
Modern Luxury Log Cabin
10 min drive
Sep 14 – 19
R50,728 ZAR for 5 nights
4.96 out of 5 average rating, 84 reviews
Top guest favorite
Home in Great Barrington
Granite Ledge, Modern home in a unique setting
10 min drive
Sep 12 – 17
R41,565 ZAR for 5 nights, originally R45,011 ZAR
4.99 out of 5 average rating, 127 reviews
Guest favorite
Guesthouse in Great Barrington
Barn Guesthouse w/ pool
10 min drive
Aug 27 – Sep 1
R26,644 ZAR for 5 nights
4.91 out of 5 average rating, 86 reviews
Superhost
Home in New Marlborough
Peaceful, Post and Beam Loft, Sleeps 9
13 min walk
Sep 20 – 25
R23,012 ZAR for 5 nights
4.85 out of 5 average rating, 87 reviews
Home in New Marlborough
INCREDIBLE LAKEFRONT 6 bed 3baths swim fish boat.
1 min walk
Aug 23 – 30
R177,731 ZAR for 7 nights, originally R194,345 ZAR
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Great Barrington
Lake House in the Heart of the Berkshires
2 min walk
Sep 2 – 7
R36,570 ZAR for 5 nights
4.95 out of 5 average rating, 43 reviews
Guest favorite
Home in Great Barrington
Lake Buel: 2 Docks, Kayaks, Patio, Fire Pit!
1 min walk
Nov 28 – Dec 3
R45,452 ZAR for 5 nights
4.96 out of 5 average rating, 23 reviews