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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 private bathroom
25–30 Oct
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5.0 out of 5 average rating, 37 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds
12–17 Sept
4.95 out of 5 average rating, 237 reviews
Top guest favourite
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Flat in Pittsfield
Mid-Berkshires
2 bedrooms, 2 queen beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
18–23 Sept
4.91 out of 5 average rating, 47 reviews
Top guest favourite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 bedrooms, 5 beds
14–19 Sept
4.95 out of 5 average rating, 75 reviews
Top guest favourite
Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
6 bedrooms, 10 beds
26 Sept – 1 Oct
4.98 out of 5 average rating, 84 reviews
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds
12–17 Sept
4.97 out of 5 average rating, 77 reviews
Home in Pittsfield
Cozy escape to the Berkshires
2 bedrooms, 2 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
17–22 Sept
4.87 out of 5 average rating, 70 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds
19–24 Oct
5.0 out of 5 average rating, 46 reviews
Guest favourite
Home in Pittsfield
Hidden Oasis in the Mountains by Evergreen Home
5 bedrooms, 8 beds
19–24 Sept
4.97 out of 5 average rating, 157 reviews
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds
12–17 Sept
4.98 out of 5 average rating, 469 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds
12–17 Sept
4.96 out of 5 average rating, 76 reviews
Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Pittsfield
Berkshire Getaway Ranch 3 acres + saltwater pool
2 bedrooms, 3 beds
13–18 Sept
4.93 out of 5 average rating, 108 reviews
Guest favourite
Home in Pittsfield
Berkshire Lakehouse - 3 bedrooms - sleeps 5
3 bedrooms, 3 beds
22–27 Sept
4.92 out of 5 average rating, 50 reviews
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds
28 Sept – 3 Oct
4.93 out of 5 average rating, 116 reviews
Guest favourite
Flat in Pittsfield
Spacious 2 bedroom downtown very nice area!
2 bedrooms, 3 beds
13–18 Sept
4.78 out of 5 average rating, 60 reviews