160 places in Great Barrington

Guest favorite
Barn in Great Barrington
Serene Renovated Barn w/ Firepit
2 beds
Apr 21 – 26
5.0 out of 5 average rating, 46 reviews
Superhost
Treehouse in New Marlborough
Double 3 Bedroom Tree House in the Berkshires
4 beds
May 5 – 10
4.92 out of 5 average rating, 84 reviews
Guest favorite
Tiny home in Chatham
Tiny House on 70 Private Acres in Hudson Valley
2 queen beds
Apr 28 – May 3
4.99 out of 5 average rating, 181 reviews
Guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bed
Apr 20 – 25
4.99 out of 5 average rating, 105 reviews
Guest favorite
Farm stay in New Lebanon
Barn Stay at Shadowbrook Farm
3 beds
Apr 21 – 26
4.95 out of 5 average rating, 184 reviews
Guest favorite
Tiny home in Chatham
HunnyHAUS: Deluxe TINY*private spa*walk to town
2 queen beds
May 5 – 10
4.99 out of 5 average rating, 307 reviews
Guest favorite
Treehouse in Tyringham
Gingerbread House Tower in the Berkshire Hills
2 beds
May 5 – 10
5.0 out of 5 average rating, 226 reviews
Guest favorite
Tiny home in Chatham
BLUSH: Boutique TINY home*private spa*walk to town
1 queen bed
Apr 28 – May 3
4.99 out of 5 average rating, 146 reviews
Guest favorite
Tiny home in Tyringham
Enchanted Tiny Tower nestled in the Berkshires
1 queen bed
Apr 28 – May 3
4.97 out of 5 average rating, 297 reviews
Guest favorite
Barn in Hillsdale
Hudson Valley Hilltop Barn
3 beds
Apr 23 – 28
4.97 out of 5 average rating, 116 reviews
Guest favorite
Room in Pittsfield
Stay with CarolynHosting for 4 years,
Equestrian retreat
Apr 22 – 27
4.96 out of 5 average rating, 157 reviews
Guest favorite
Farm stay in Hillsdale
FARM HOUSE on Old Horse Farm!
7 beds
Apr 20 – 25
4.97 out of 5 average rating, 62 reviews
Guest favorite
Farm stay in Copake
Hudson Valley Charming Farm House 70 acre farm
9 beds
Apr 20 – 25
4.96 out of 5 average rating, 28 reviews
Guest favorite
Farm stay in Worthington
Like sleeping on a cloud
3 beds
Aug 26 – 31
5.0 out of 5 average rating, 9 reviews
Guest favorite
Farm stay in Blandford
Freeland Brook Farm - stunning Berkshires view
3 beds
May 5 – 10
5.0 out of 5 average rating, 9 reviews
Guest favorite
Farm stay in Ancram
Relaxing secluded stay with loving social animals.
2 beds
May 29 – Jun 3
4.95 out of 5 average rating, 264 reviews
Guest favorite
Farm stay in West Simsbury
Flamig Farm Staycation
4 beds
Aug 25 – 30
4.95 out of 5 average rating, 429 reviews
Guest favorite
Farm stay in Salisbury
The Loft with a View
1 bed
May 5 – 10
5.0 out of 5 average rating, 35 reviews