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Search results; Over 1,000 homes in Pittsfield

Descriptions are based on details hosts provide
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 private bathroom
6–11 Sept
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4.99 out of 5 average rating, 315 reviews
Top guest favourite
Room in Pittsfield
Themed room in a Queen Anne Victorian
2 beds, 3 bathrooms
26–31 Jul
5.0 out of 5 average rating, 17 reviews
Guest favourite
Room in Pittsfield
Drag-themed Queen Anne Victorian mansion
1 bed, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 48 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 86 reviews
Top guest favourite
Home in Pittsfield
Pond-front with a fireplace and kayak
2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 26 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 317 reviews
Top guest favourite
Room in Pittsfield
Spacious suite with homemade breakfast included
2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 460 reviews
Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
4.84 out of 5 average rating, 194 reviews
Guest favourite
Home in Pittsfield
Grand piano and game room near Tanglewood
3 bedrooms, 5 beds, 2 bathrooms
26–31 Jul
4.95 out of 5 average rating, 218 reviews
Home in Lenox
7 Minute Walk to Tanglewood from New 2BR Home
2 bedrooms, 2 queen beds, 1.5 bathrooms
25–30 Jul
New place to stay
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
23–28 Aug
4.77 out of 5 average rating, 31 reviews
Guest favourite
Home in Lenox
Newly renovated, 10 minutes from Tanglewood
2 bedrooms, 2 beds, 1 bathroom
16–21 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Hinsdale
Berkshire Lake-side Retreat
2 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 14 reviews
Room in Pittsfield
1800s artist’s home near downtown
1 double bed, 1.5 bathrooms
26–31 Aug
4.84 out of 5 average rating, 87 reviews
Guest favourite
Home in Pittsfield
A Ray of Sunshine-Lakefront-New Construction- ski
5 bedrooms, 4.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 35 reviews
Guest favourite
Resort in Hancock
Ski resort suite in the Berkshires
1 bedroom, 2 beds, 1 bathroom
16–21 Jul
4.72 out of 5 average rating, 267 reviews
Guest favourite
Room in Pittsfield
Sunny Room in Downtown Victorian
1 bed, 2 bathrooms
21–26 Jul
4.78 out of 5 average rating, 18 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 603 reviews
Guest favourite
Townhouse in Hancock
Ski-in/ski-out with pool and hot tub
2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 12 reviews