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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 private bathroom
23–28 Aug
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4.99 out of 5 average rating, 314 reviews
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
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
5.0 out of 5 average rating, 17 reviews, 2 beds, 3 bathrooms
30 Aug – 4 Sept
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
4.92 out of 5 average rating, 48 reviews, 1 bed, 2 bathrooms
23–28 Aug
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
5.0 out of 5 average rating, 83 reviews, 1 queen bed, 1 bathroom
24–29 Aug
Room in Pittsfield
The Yellow Room
4.84 out of 5 average rating, 87 reviews, 1 double bed, 1.5 bathrooms
27 Jul – 1 Aug
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
4.65 out of 5 average rating, 34 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Jul
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
4.98 out of 5 average rating, 457 reviews, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
4.93 out of 5 average rating, 105 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
Guest favourite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
4.93 out of 5 average rating, 133 reviews, 3 bedrooms, 4 beds, 1 bathroom
28 Oct – 2 Nov
Top guest favourite
Home in Lanesborough
The Pond House
4.96 out of 5 average rating, 50 reviews, 3 bedrooms, 4 beds, 1 bathroom
9–14 Dec
Guest favourite
Home in Pittsfield
Elmer Estate
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Nov
Place to stay in Pittsfield
Cozy room in Pittsfield #2
1 bedroom, 1 bed, 1.5 bathrooms
11–16 Jul
Guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
4.91 out of 5 average rating, 124 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
4.96 out of 5 average rating, 199 reviews, 2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
Guest favourite
Flat in Pittsfield
Marie's Place
4.91 out of 5 average rating, 316 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Room in Pittsfield
Modern, Spacious Master Bedroom and Bathroom
4.92 out of 5 average rating, 99 reviews, 1 king bed, 1.5 bathrooms
13–18 Jul
Top guest favourite
Room in Pittsfield
Creative Haven in the Berkshires - Nest Room
5.0 out of 5 average rating, 25 reviews, 1 queen bed, 1 bathroom
22–27 Aug
Guest favourite
Home in Lenox
Cozy Home in Lenox
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Jul