127 places in Pittsfield

Guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bed
Apr 18 – 23
4.99 out of 5 average rating, 105 reviews
Farm stay in New Lebanon
Historic 1789 Shaker Farmhouse in Berkshires
7 beds
Apr 18 – 23
5.0 out of 5 average rating, 3 reviews
Farm stay in New Lebanon
NEW RENO Chalet-style farm loft near Tanglewood
3 beds
Apr 19 – 24
4.75 out of 5 average rating, 4 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, 225 reviews
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
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
Camper/RV in Lee
"Glamping" getaway in the beautiful Berkshires
5 beds
May 1 – 6
5.0 out of 5 average rating, 117 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, 180 reviews
Superhost
Room in Stephentown
Stay with ThomasReal estate,
A Stay at the Homestead 3
Apr 19 – 24
4.9 out of 5 average rating, 10 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
Tiny home in Chatham
Sugar Shack - 300 square feet of pure sweetness.
1 queen bed
Apr 28 – May 3
4.99 out of 5 average rating, 269 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
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
Room in Stephentown
Stay with ThomasReal estate,
A Stay at the Homestead
Apr 28 – May 3
4.83 out of 5 average rating, 18 reviews
Guest favorite
Barn in Troy
Irish-Inspired Hunt Box Retreat for Horse Lovers
Apr 18 – 23
5.0 out of 5 average rating, 7 reviews
Guest favorite
Farm stay in Averill Park
Modern Country Farmhouse, Walking Distance to Lake
4 beds
Apr 19 – 24
4.94 out of 5 average rating, 16 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
Earthen home in West Sand Lake
The Hobbit House at June Farms
1 king bed
Jul 28 – Aug 2
4.98 out of 5 average rating, 150 reviews