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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Summer on the Lake - Berkshires near Tanglewood
3 bedrooms, 4 beds, 2 private bathrooms
13–18 Sept
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4.96 out of 5 average rating, 76 reviews
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds
8–13 Sept
5.0 out of 5 average rating, 4 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
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
20–25 Sept
5.0 out of 5 average rating, 37 reviews
Flat in Pittsfield
Mid-Berkshires
2 bedrooms, 2 queen beds
11–16 Sept
5.0 out of 5 average rating, 3 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, 236 reviews
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
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
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
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
Charming Historic Retreat, <15 min from Lenox
4 bedrooms, 6 beds
20–25 Sept
5.0 out of 5 average rating, 15 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
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
Marie's Place, Unit 1
3 bedrooms, 3 beds
8–13 Sept
4.97 out of 5 average rating, 130 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
12–17 Sept
4.92 out of 5 average rating, 329 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
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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
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds
10–15 Sept
4.94 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
10–15 Sept
4.95 out of 5 average rating, 75 reviews