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Search results; Over 1,000 homes in Pittsfield

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Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 private bathroom
20–25 Sept
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4.65 out of 5 average rating, 51 reviews
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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, 85 reviews
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Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 240 reviews
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Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 37 reviews
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Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 7 reviews
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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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Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds, 4 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 47 reviews
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Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
21–26 Sept
4.92 out of 5 average rating, 48 reviews
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Home in Pittsfield
Charming Historic Retreat, <15 min from Lenox
4 bedrooms, 6 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 15 reviews
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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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Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds, 1 bathroom
21–26 Oct
4.98 out of 5 average rating, 469 reviews
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Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 78 reviews
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Home in Pittsfield
Berkshire Views
6 bedrooms, 7 beds, 4 bathrooms
11–16 Oct
5.0 out of 5 average rating, 19 reviews
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Home in Pittsfield
Cozy escape to the Berkshires
2 bedrooms, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 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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Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
4–9 Oct
4.88 out of 5 average rating, 74 reviews
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Home in Pittsfield
Hidden Oasis in the Mountains by Evergreen Home
5 bedrooms, 8 beds, 3 bathrooms
20–25 Sept
4.97 out of 5 average rating, 157 reviews
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Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
20–25 Sept
4.85 out of 5 average rating, 54 reviews
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Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
29 Sept – 4 Oct
4.96 out of 5 average rating, 76 reviews