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Search results; Over 1,000 homes in Pittsfield

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Guest favourite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
3 bedrooms, 4 beds, 1 private bathroom
27 Oct – 1 Nov
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4.93 out of 5 average rating, 136 reviews
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Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
25–30 Oct
4.95 out of 5 average rating, 240 reviews
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Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
4–9 Oct
4.92 out of 5 average rating, 50 reviews
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Top guest favourite
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 7 reviews
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Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.65 out of 5 average rating, 52 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
4–9 Oct
4.98 out of 5 average rating, 85 reviews
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Top guest favourite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 bedrooms, 5 beds, 2 bathrooms
13–18 Oct
4.95 out of 5 average rating, 75 reviews
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Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
4–9 Oct
4.88 out of 5 average rating, 75 reviews
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Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 38 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
1–6 Oct
4.94 out of 5 average rating, 47 reviews
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Guest favourite
Home in Pittsfield
The Fox Hollow Estate
6 bedrooms, 6 beds, 6 bathrooms
1–6 Nov
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Home in Pittsfield
Berkshire Estate
9 bedrooms, 10 beds, 4.5 bathrooms
7–12 Oct
4.86 out of 5 average rating, 22 reviews
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Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
3–8 Oct
4.97 out of 5 average rating, 78 reviews
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Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Oct
4.96 out of 5 average rating, 77 reviews
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Guest favourite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 26 reviews
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Top guest favourite
Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 26 reviews
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Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
16–21 Oct
4.86 out of 5 average rating, 56 reviews
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Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Oct
5.0 out of 5 average rating, 27 reviews
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Top guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 bathrooms
4–9 Oct
4.95 out of 5 average rating, 43 reviews