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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Berkshire Getaway Ranch 3 acres + saltwater pool
2 bedrooms, 3 beds, 2 private bathrooms
22–27 Aug
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4.92 out of 5 average rating, 106 reviews
Superhost
Room in Pittsfield
Cozy Corner Room in Downtown Victorian
1 bed, 2.5 bathrooms
24–29 Aug
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
5.0 out of 5 average rating, 87 reviews, 1 queen bed, 1 bathroom
24–29 Aug
Guest favourite
Room in Pittsfield
Sunny Room in Downtown Victorian
4.79 out of 5 average rating, 19 reviews, 1 bed, 2 bathrooms
6–11 Aug
Room in Pittsfield
The Yellow Room
4.84 out of 5 average rating, 88 reviews, 1 double bed, 1.5 bathrooms
26–31 Aug
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
4.83 out of 5 average rating, 24 reviews, 2 beds, 3 bathrooms
30 Aug – 4 Sept
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
4.68 out of 5 average rating, 37 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
4.91 out of 5 average rating, 129 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Top guest favourite
Room in Pittsfield
Creative Haven in the Berkshires - Nest Room
5.0 out of 5 average rating, 27 reviews, 1 queen bed, 1 bathroom
22–27 Aug
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
4.99 out of 5 average rating, 320 reviews, 1 bedroom, 1 bed, 1 bathroom
6–11 Sept
Guest favourite
Flat in Pittsfield
Comfortable Pittsfield Loft
4.92 out of 5 average rating, 51 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 May
Room in Pittsfield
Cozy room in Pittsfield #2
5.0 out of 5 average rating, 4 reviews, 1 double bed, 1.5 bathrooms
1–6 Aug
Top guest favourite
Room in Pittsfield
Airy Queen Bedroom with Couch, Pittsfield
4.96 out of 5 average rating, 73 reviews, 1 queen bed, 1 bathroom
2–7 Aug
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
4.98 out of 5 average rating, 464 reviews, 2 beds, 1 bathroom
23–28 Aug
Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
4.84 out of 5 average rating, 194 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
Top guest favourite
Flat in Lenox
Main Street Delight One Bedroom Apartment
4.98 out of 5 average rating, 90 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Oct
Guest favourite
Cabin in Cheshire
Private Paradise in the Berkshires
4.9 out of 5 average rating, 174 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Flat in Pittsfield
Beautiful Victorian Apartment on Bartlett Ave
3 bedrooms, 3 beds, 1.5 bathrooms
1–6 Aug
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
5.0 out of 5 average rating, 42 reviews, 4 bedrooms, 4 beds, 1.5 bathrooms
24–29 Aug