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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
9–14 Aug
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4.96 out of 5 average rating, 225 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
23–28 Aug
4.82 out of 5 average rating, 38 reviews
Superhost
Room in Pittsfield
Cozy Corner Room in Downtown Victorian
1 bed, 2.5 bathrooms
14–19 Sept
Room in Pittsfield
The Yellow Room
1 double bed, 1.5 bathrooms
29 Aug – 3 Sept
4.84 out of 5 average rating, 90 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
30 Aug – 4 Sept
4.85 out of 5 average rating, 26 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
22–27 Aug
4.71 out of 5 average rating, 41 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 87 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
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
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, 613 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, 31 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
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
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.92 out of 5 average rating, 322 reviews
Room in Pittsfield
Cozy room in Pittsfield #2
1 double bed, 1.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 4 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, 322 reviews
Top guest favourite
Flat in East Chatham
Bennett Abode
1 bedroom, 1 double bed, 1.5 bathrooms
23–28 Aug
4.96 out of 5 average rating, 178 reviews
Top guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 134 reviews
Flat in Pittsfield
Spacious Green 2 bedroom Downtown
2 bedrooms, 4 beds, 1 bathroom
23–28 Aug
4.81 out of 5 average rating, 52 reviews