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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Ski the Berkshires at Hygge House on Richmond Pond
3 bedrooms, 4 beds, 2 private bathrooms
26 Jul – 2 Aug
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4.96 out of 5 average rating, 73 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
4.92 out of 5 average rating, 49 reviews, 1 bed, 2 bathrooms
23–28 Aug
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
5.0 out of 5 average rating, 18 reviews, 2 beds, 3 bathrooms
30 Aug – 4 Sept
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
4.99 out of 5 average rating, 315 reviews, 1 bedroom, 1 bed, 1 bathroom
6–11 Sept
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
Home in Pittsfield
Cantabile life in the Berkshires
4.95 out of 5 average rating, 218 reviews, 3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
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
Home in Lenox
7 Minute Walk to Tanglewood from New 2BR Home
New place to stay, 2 bedrooms, 2 beds, 1.5 bathrooms
25–30 Jul
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
Guest favourite
Flat in Pittsfield
Marie's Place
4.92 out of 5 average rating, 318 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
5.0 out of 5 average rating, 41 reviews, 4 bedrooms, 4 beds, 1.5 bathrooms
24–29 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
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
Room in Pittsfield
The Yellow Room
4.84 out of 5 average rating, 88 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 Lenox
Cozy Home in Lenox
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
20–25 Jul
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
Home in Lanesborough
The Pond House
4.96 out of 5 average rating, 51 reviews, 3 bedrooms, 4 beds, 1 bathroom
20–25 Nov
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