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Search results; Over 1,000 homes in Pittsfield

Serviced apartment in Pittsfield
One Bedroom Apartment with a full kitchen
1 bedroom, 2 beds, 1 bathroom
6–11 Jul
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4.83 out of 5 average rating, 6 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
5.0 out of 5 average rating, 14 reviews, 2 beds, 3 bathrooms
12–17 Jul
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
Romantic King Room in Downtown Victorian
4.94 out of 5 average rating, 47 reviews, 1 bed, 2 bathrooms
12–17 Jul
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
5.0 out of 5 average rating, 80 reviews, 1 queen bed, 1 bathroom
24–29 Aug
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
4.98 out of 5 average rating, 455 reviews, 2 beds, 1 bathroom
23–28 Aug
Room in Pittsfield
The Yellow Room
4.84 out of 5 average rating, 85 reviews, 1 double bed, 1.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
4.93 out of 5 average rating, 104 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
4.99 out of 5 average rating, 310 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Top guest favourite
Home in Lanesborough
The Pond House
4.96 out of 5 average rating, 49 reviews, 3 bedrooms, 4 beds, 1 bathroom
9–14 Dec
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
4.94 out of 5 average rating, 35 reviews, 3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
Guest favourite
Home in Pittsfield
Elmer Estate
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 3 beds, 1 bathroom
21–26 Oct
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
16–21 Sept
Guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
4.92 out of 5 average rating, 120 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
4.95 out of 5 average rating, 214 reviews, 3 bedrooms, 5 beds, 2 bathrooms
6–11 Jul
Guest favourite
Flat in Pittsfield
Beautiful & Serene Getaway
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 2 beds, 1 bathroom
5–10 Jul
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
4.96 out of 5 average rating, 197 reviews, 2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
Guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
4.97 out of 5 average rating, 115 reviews, 3 bedrooms, 3 beds, 1 bathroom
4–9 Jul