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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
6 bedrooms, 10 beds, 4.5 private bathrooms
26 Sept – 1 Oct
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4.98 out of 5 average rating, 82 reviews
Superhost
Room in Pittsfield
Cozy Corner Room in Downtown Victorian
1 bed, 2.5 bathrooms
14–19 Sept
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
30 Aug – 4 Sept
4.86 out of 5 average rating, 28 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
24–29 Sept
5.0 out of 5 average rating, 88 reviews
Room in Pittsfield
The Yellow Room
1 double bed, 1.5 bathrooms
28 Sept – 3 Oct
4.84 out of 5 average rating, 90 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
6–11 Sept
4.83 out of 5 average rating, 40 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
4.96 out of 5 average rating, 226 reviews
Room in Pittsfield
Cozy room in Pittsfield #2
1 double bed, 1.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Room in Pittsfield
Sunny Room in Downtown Victorian
1 bed, 2 bathrooms
17–22 Aug
4.75 out of 5 average rating, 20 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
22–27 Aug
4.65 out of 5 average rating, 43 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
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, 464 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 615 reviews
Top guest favourite
Room in Becket
East b.r. in upstairs suite of open plan home
1 bathroom
9–14 Aug
4.87 out of 5 average rating, 259 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 bathroom
25–30 Sept
4.99 out of 5 average rating, 325 reviews
Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
4.81 out of 5 average rating, 209 reviews
Top guest favourite
Room in Pittsfield
Pittsfield. Large queen bedroom, second floor.
1 queen bed, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Flat in New Lebanon
Folk Art Studio: 1-bedroom near the Berkshires
1 bedroom, 2 beds, 1 bathroom
5–10 Sept
5.0 out of 5 average rating, 31 reviews