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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 private bathrooms
26–31 Jul
,
4.95 out of 5 average rating, 218 reviews
Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 bedrooms, 2 beds
1–6 Nov
4.84 out of 5 average rating, 194 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
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
24–29 Aug
5.0 out of 5 average rating, 86 reviews
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews
Room in Pittsfield
The Yellow Room
1 double bed
23–28 Aug
4.84 out of 5 average rating, 87 reviews
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds
23–28 Aug
4.98 out of 5 average rating, 457 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
13–18 Jul
4.66 out of 5 average rating, 35 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed
23–28 Aug
4.99 out of 5 average rating, 315 reviews
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds
7–12 Sept
4.93 out of 5 average rating, 105 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
1–6 Aug
4.77 out of 5 average rating, 31 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds
9–14 Dec
4.96 out of 5 average rating, 50 reviews
Guest favourite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
3 bedrooms, 4 beds
28 Oct – 2 Nov
4.93 out of 5 average rating, 133 reviews
Guest favourite
Room in Pittsfield
Sunny Room in Downtown Victorian
1 bed
21–26 Jul
4.78 out of 5 average rating, 18 reviews
Guest favourite
Home in Lenox
Cozy Home in Lenox
2 bedrooms, 2 beds
14–19 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Room in Pittsfield
Modern, Spacious Master Bedroom and Bathroom
1 king bed
13–18 Jul
4.92 out of 5 average rating, 99 reviews
Guest favourite
Home in Pittsfield
Hidden Oasis in the Mountains by Evergreen Home
5 bedrooms, 8 beds
27 Jul – 1 Aug
4.97 out of 5 average rating, 152 reviews
Flat in Pittsfield
Beautiful Victorian Apartment on Bartlett Ave
3 bedrooms, 3 beds
19–24 Jul
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
9–14 Aug
4.91 out of 5 average rating, 316 reviews