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Search results; Over 1,000 homes in Pittsfield

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
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
26–31 Jul
5.0 out of 5 average rating, 17 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
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 48 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
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
Large guest suite w/private bath in the Berkshires
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
Room in Pittsfield
The Yellow Room
1 double bed, 1.5 bathrooms
23–28 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
Top guest favourite
Home in Hinsdale
Berkshire Lake-side Retreat
2 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
26–31 Jul
4.95 out of 5 average rating, 218 reviews
Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Aug
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Lenox
Cozy Home in Lenox
2 bedrooms, 2 beds, 1 bathroom
14–19 Jul
5.0 out of 5 average rating, 7 reviews
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
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 41 reviews
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 12 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
Guest favourite
Resort in Hancock
Country Inn Suite at Jiminy Peak - No fees added
1 bedroom, 2 beds, 1 bathroom
14–19 Jul
4.72 out of 5 average rating, 267 reviews