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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
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds
7–12 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds
11–16 Sept
4.95 out of 5 average rating, 234 reviews
Flat in Pittsfield
Mid-Berkshires
2 bedrooms, 2 queen beds
11–16 Sept
New place to stay
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
17–22 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
9–14 Sept
4.95 out of 5 average rating, 75 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds
9–14 Sept
5.0 out of 5 average rating, 46 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
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds
9–14 Sept
4.94 out of 5 average rating, 47 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
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds
28 Sept – 3 Oct
4.93 out of 5 average rating, 116 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, 76 reviews
Top guest favourite
Home in Pittsfield
Charming Historic Retreat, <15 min from Lenox
4 bedrooms, 6 beds
20–25 Sept
5.0 out of 5 average rating, 15 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
Blue Suite in Downtown Victorian
1 bed
20–25 Sept
4.85 out of 5 average rating, 52 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
10–15 Sept
4.87 out of 5 average rating, 70 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, 466 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
8–13 Sept
4.64 out of 5 average rating, 50 reviews
Guest favourite
Home in Pittsfield
Dancing Horse Lodge
3 bedrooms, 3 beds
11–16 Sept
4.87 out of 5 average rating, 330 reviews