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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
6–11 Sept
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4.99 out of 5 average rating, 315 reviews
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
26–31 Jul
Guest favourite
Home in Pittsfield
A Ray of Sunshine-Lakefront-New Construction- ski
5.0 out of 5 average rating, 35 reviews, 5 bedrooms, 4.5 bathrooms
26–31 Jul
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
5.0 out of 5 average rating, 41 reviews, 4 bedrooms, 4 beds, 1.5 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, 86 reviews, 1 queen bed, 1 bathroom
24–29 Aug
Top guest favourite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
4.95 out of 5 average rating, 75 reviews, 5 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
4.95 out of 5 average rating, 218 reviews, 3 bedrooms, 5 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
4.98 out of 5 average rating, 81 reviews, 6 bedrooms, 10 beds, 4.5 bathrooms
26 Sept – 1 Oct
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
4.93 out of 5 average rating, 105 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 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
Home in Pittsfield
Cozy cottage on peaceful pond
5.0 out of 5 average rating, 26 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
Home in Lanesborough
New built - Split level house in the Berkshires
3 bedrooms, 5 beds, 3 bathrooms
21–26 Jul
Guest favourite
Home in Pittsfield
Hidden Oasis in the Mountains by Evergreen Home
4.97 out of 5 average rating, 152 reviews, 5 bedrooms, 8 beds, 3 bathrooms
27 Jul – 1 Aug
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
4.98 out of 5 average rating, 460 reviews, 2 beds, 1 bathroom
23–28 Aug
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
4.66 out of 5 average rating, 35 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Guest favourite
Flat in Pittsfield
Marie's Place
4.91 out of 5 average rating, 317 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
4.94 out of 5 average rating, 36 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
4.97 out of 5 average rating, 65 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
23–28 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