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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Hidden Oasis in the Mountains by Evergreen Home
5 bedrooms, 8 beds, 3 private bathrooms
19–24 Sept
,
4.97 out of 5 average rating, 154 reviews
Superhost
Room in Pittsfield
Cozy Corner Room in Downtown Victorian
1 bed
2–7 Sept
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, 87 reviews
Room in Pittsfield
The Yellow Room
1 double bed
26–31 Aug
4.84 out of 5 average rating, 88 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
23–28 Aug
4.8 out of 5 average rating, 35 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
30 Aug – 4 Sept
4.83 out of 5 average rating, 24 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
2–7 Aug
4.68 out of 5 average rating, 37 reviews
Guest favourite
Room in Pittsfield
Sunny Room in Downtown Victorian
1 bed
22–27 Aug
4.79 out of 5 average rating, 19 reviews
Top guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 queen bed
7–12 Sept
4.92 out of 5 average rating, 131 reviews
Guest favourite
Flat in Pittsfield
Comfortable Pittsfield Loft
1 bedroom, 1 queen bed
1–6 May
4.92 out of 5 average rating, 51 reviews
Top guest favourite
Room in Pittsfield
Creative Haven in the Berkshires - Nest Room
1 queen bed
23–28 Sept
5.0 out of 5 average rating, 27 reviews
Room in Pittsfield
Cozy room in Pittsfield #2
1 double bed
1–6 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
9–14 Aug
4.92 out of 5 average rating, 320 reviews
Top guest favourite
Room in Pittsfield
Pittsfield. Large queen bedroom, second floor.
1 queen bed
1–6 Aug
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed
6–11 Sept
4.99 out of 5 average rating, 321 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
Large guest suite w/private bath in the Berkshires
2 beds
23–28 Aug
4.98 out of 5 average rating, 464 reviews
Flat in Pittsfield
Spacious Green 2 bedroom Downtown
2 bedrooms, 4 beds
9–14 Aug
4.8 out of 5 average rating, 51 reviews
Guest favourite
Cabin in Cheshire
Private Paradise in the Berkshires
1 bedroom, 1 bed
26–31 Aug
4.9 out of 5 average rating, 174 reviews