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Search results; Over 1,000 homes in Pittsfield

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Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
1 bedroom, 2 beds, 1 private bathroom
12–17 Sept
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4.98 out of 5 average rating, 466 reviews
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Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 37 reviews
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Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
6–11 Sept
4.9 out of 5 average rating, 40 reviews
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Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 45 reviews
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Top guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
4.96 out of 5 average rating, 230 reviews
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Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
7–12 Sept
4.9 out of 5 average rating, 63 reviews
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Top guest favourite
Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
6 bedrooms, 10 beds, 4.5 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 83 reviews
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Home in Pittsfield
Berkshire Lakehouse - 3 bedrooms - sleeps 5
3 bedrooms, 3 beds, 1 bathroom
22–27 Sept
4.92 out of 5 average rating, 50 reviews
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Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 129 reviews
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Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
6–11 Sept
4.85 out of 5 average rating, 47 reviews
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Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
6–11 Sept
New place to stay
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Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 115 reviews
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Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 26 reviews
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Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Sept
4.97 out of 5 average rating, 74 reviews
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Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.63 out of 5 average rating, 49 reviews
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Home in Pittsfield
Berkshire Views
6 bedrooms, 7 beds, 4 bathrooms
13–18 Sept
5.0 out of 5 average rating, 19 reviews
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Top guest favourite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds, 4 bathrooms
2–7 Sept
4.94 out of 5 average rating, 47 reviews
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Home in Pittsfield
Cozy escape to the Berkshires
2 bedrooms, 2 beds, 1.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Pittsfield
Dancing Horse Lodge
3 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.87 out of 5 average rating, 330 reviews