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pittsfield ma
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19
127 places in Pittsfield
Guest favorite
Guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bed
1 bed
Apr 18 – 23
Apr 18 – 23
$106
night
$106 per night
4.99 out of 5 average rating, 105 reviews
4.99 (105)
Farm stay in New Lebanon
Historic 1789 Shaker Farmhouse in Berkshires
7 beds
7 beds
Apr 18 – 23
Apr 18 – 23
$167
$148
night
$148 per night, originally $167
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Farm stay in New Lebanon
NEW RENO Chalet-style farm loft near Tanglewood
3 beds
3 beds
Apr 19 – 24
Apr 19 – 24
$79
night
$79 per night
4.75 out of 5 average rating, 4 reviews
4.75 (4)
Guest favorite
Guest favorite
Treehouse in Tyringham
Gingerbread House Tower in the Berkshire Hills
2 beds
2 beds
May 5 – 10
May 5 – 10
$297
night
$297 per night
5.0 out of 5 average rating, 225 reviews
5.0 (225)
Guest favorite
Guest favorite
Barn in Great Barrington
Serene Renovated Barn w/ Firepit
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$178
night
$178 per night
5.0 out of 5 average rating, 46 reviews
5.0 (46)
Guest favorite
Guest favorite
Farm stay in New Lebanon
Barn Stay at Shadowbrook Farm
3 beds
3 beds
Apr 21 – 26
Apr 21 – 26
$192
night
$192 per night
4.95 out of 5 average rating, 184 reviews
4.95 (184)
Guest favorite
Guest favorite
Camper/RV in Lee
"Glamping" getaway in the beautiful Berkshires
5 beds
5 beds
May 1 – 6
May 1 – 6
$168
night
$168 per night
5.0 out of 5 average rating, 117 reviews
5.0 (117)
Guest favorite
Guest favorite
Tiny home in Chatham
Tiny House on 70 Private Acres in Hudson Valley
2 queen beds
2 queen beds
Apr 28 – May 3
Apr 28 – May 3
$149
night
$149 per night
4.99 out of 5 average rating, 180 reviews
4.99 (180)
Superhost
Superhost
10
Reviews
4.9
Rating
6
Years hosting
Room in Stephentown
Stay with Thomas
Stay with Thomas
Real estate
,
·
Real estate
A Stay at the Homestead 3
Apr 19 – 24
Apr 19 – 24
$69
night
$69 per night
4.9 out of 5 average rating, 10 reviews
4.9 (10)
Guest favorite
Guest favorite
157
Reviews
4.96
Rating
4
Years hosting
Room in Pittsfield
Stay with Carolyn
Stay with Carolyn
Hosting for 4 years
,
·
Hosting for 4 years
Equestrian retreat
Apr 22 – 27
Apr 22 – 27
$95
night
$95 per night
4.96 out of 5 average rating, 157 reviews
4.96 (157)
Guest favorite
Guest favorite
Tiny home in Chatham
Sugar Shack - 300 square feet of pure sweetness.
1 queen bed
1 queen bed
Apr 28 – May 3
Apr 28 – May 3
$188
night
$188 per night
4.99 out of 5 average rating, 269 reviews
4.99 (269)
Guest favorite
Guest favorite
Farm stay in Worthington
Like sleeping on a cloud
3 beds
3 beds
Aug 26 – 31
Aug 26 – 31
$205
night
$205 per night
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Guest favorite
Guest favorite
Tiny home in Chatham
HunnyHAUS: Deluxe TINY*private spa*walk to town
2 queen beds
2 queen beds
May 5 – 10
May 5 – 10
$205
night
$205 per night
4.99 out of 5 average rating, 307 reviews
4.99 (307)
Guest favorite
Guest favorite
18
Reviews
4.83
Rating
6
Years hosting
Room in Stephentown
Stay with Thomas
Stay with Thomas
Real estate
,
·
Real estate
A Stay at the Homestead
Apr 28 – May 3
Apr 28 – May 3
$69
night
$69 per night
4.83 out of 5 average rating, 18 reviews
4.83 (18)
Guest favorite
Guest favorite
Barn in Troy
Irish-Inspired Hunt Box Retreat for Horse Lovers
Apr 18 – 23
Apr 18 – 23
$259
$220
night
$220 per night, originally $259
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Guest favorite
Guest favorite
Farm stay in Averill Park
Modern Country Farmhouse, Walking Distance to Lake
4 beds
4 beds
Apr 19 – 24
Apr 19 – 24
$199
$177
night
$177 per night, originally $199
4.94 out of 5 average rating, 16 reviews
4.94 (16)
Guest favorite
Guest favorite
Tiny home in Tyringham
Enchanted Tiny Tower nestled in the Berkshires
1 queen bed
1 queen bed
Apr 28 – May 3
Apr 28 – May 3
$198
night
$198 per night
4.97 out of 5 average rating, 297 reviews
4.97 (297)
Guest favorite
Guest favorite
Earthen home in West Sand Lake
The Hobbit House at June Farms
1 king bed
1 king bed
Jul 28 – Aug 2
Jul 28 – Aug 2
$303
night
$303 per night
4.98 out of 5 average rating, 150 reviews
4.98 (150)
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