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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
Superhost
Room in Pittsfield
Cozy Corner Room in Downtown Victorian
1 bed
14–19 Sept
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
30 Aug – 4 Sept
4.86 out of 5 average rating, 28 reviews
Room in Pittsfield
The Yellow Room
1 double bed
29 Aug – 3 Sept
4.84 out of 5 average rating, 90 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
22–27 Aug
4.65 out of 5 average rating, 43 reviews
Superhost
Room in Pittsfield
Sunny Room in Downtown Victorian
1 bed
17–22 Aug
4.75 out of 5 average rating, 20 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
6–11 Sept
4.83 out of 5 average rating, 40 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, 464 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
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed
24–29 Sept
5.0 out of 5 average rating, 87 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
9–14 Aug
4.92 out of 5 average rating, 322 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed
30 Aug – 4 Sept
4.97 out of 5 average rating, 614 reviews
Guest favourite
Farm stay in New Lebanon
NEW RENO - Chalet-style farm loft near Tanglewood
1 bedroom, 3 beds
9–14 Aug
4.91 out of 5 average rating, 70 reviews
Flat in Pittsfield
Spacious Green 2 bedroom Downtown
2 bedrooms, 4 beds
23–28 Aug
4.81 out of 5 average rating, 52 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed
25–30 Sept
4.99 out of 5 average rating, 325 reviews
Top guest favourite
Room in Pittsfield
Pittsfield. Large queen bedroom, second floor.
1 queen bed
9–14 Aug
4.96 out of 5 average rating, 48 reviews
Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
2 bedrooms, 3 beds
8–13 Sept
4.81 out of 5 average rating, 209 reviews
Room in Pittsfield
Cozy room in Pittsfield #2
1 double bed
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
26–31 Oct
5.0 out of 5 average rating, 32 reviews