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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
5.0 out of 5 average rating, 17 reviews, 2 beds, 3 bathrooms
26–31 Jul
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
4.92 out of 5 average rating, 48 reviews, 1 bed, 2 bathrooms
23–28 Aug
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
5.0 out of 5 average rating, 86 reviews, 1 queen bed, 1 bathroom
24–29 Aug
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
5.0 out of 5 average rating, 26 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
Guest favourite
Flat in Pittsfield
Newly renovated, minutes from ski and downtown
4.91 out of 5 average rating, 317 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
4.98 out of 5 average rating, 460 reviews, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4.99 out of 5 average rating, 311 reviews, 3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
Guest favourite
Home in Pittsfield
Grand piano and game room near Tanglewood
4.95 out of 5 average rating, 218 reviews, 3 bedrooms, 5 beds, 2 bathrooms
26–31 Jul
Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
4.84 out of 5 average rating, 194 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
Guest favourite
Home in Lenox
Newly renovated, 10 minutes from Tanglewood
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Jul
Home in Lenox
Walk to Tanglewood from 2 acres
New place to stay, 2 bedrooms, 2 beds, 1.5 bathrooms
25–30 Jul
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
4.77 out of 5 average rating, 31 reviews, 1 bed, 2 bathrooms
23–28 Aug
Room in Pittsfield
The Yellow Room
4.84 out of 5 average rating, 87 reviews, 1 double bed, 1.5 bathrooms
26–31 Aug
Top guest favourite
Home in Hinsdale
Berkshire Lake-side Retreat
5.0 out of 5 average rating, 14 reviews, 2 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Guest favourite
Home in Pittsfield
A Ray of Sunshine-Lakefront-New Construction- ski
5.0 out of 5 average rating, 35 reviews, 5 bedrooms, 4.5 bathrooms
26–31 Jul
Guest favourite
Guest suite in Lenox
High Above Cliffwood (Full Apartment)
5.0 out of 5 average rating, 21 reviews, 1 bedroom, 1 bed, 1 bathroom
31 Jul – 5 Aug
Flat in Pittsfield
Spacious Green 2 bedroom Downtown
4.82 out of 5 average rating, 49 reviews, 2 bedrooms, 4 beds, 1 bathroom
26–31 Jul
Top guest favourite
Flat in Pittsfield
Quiet Berkshires base near ski and trails
4.93 out of 5 average rating, 105 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept