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Search results; Over 1,000 homes in Pittsfield

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Guest favourite
Home in Pittsfield
Berkshire Getaway Ranch 3 acres + saltwater pool
2 bedrooms, 3 beds, 2 private bathrooms
4–9 Oct
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4.93 out of 5 average rating, 109 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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Superhost
Home in Pittsfield
The Sunset Fern Cliff House
2 bedrooms, 2 beds, 1 bathroom
3–8 Oct
New place to stay
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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
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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Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.66 out of 5 average rating, 53 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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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
Large guest suite w/private bath in the Berkshires
2 beds, 1 bathroom
21–26 Oct
4.98 out of 5 average rating, 470 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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Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
4–9 Oct
4.97 out of 5 average rating, 78 reviews
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Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 bedrooms, 2 beds, 1.5 bathrooms
2–7 Oct
4.84 out of 5 average rating, 194 reviews
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Guest favourite
Home in Pittsfield
Berkshire Lakehouse - 3 bedrooms - sleeps 5
3 bedrooms, 3 beds, 1 bathroom
6–11 Oct
4.92 out of 5 average rating, 50 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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Guest favourite
Flat in Pittsfield
Spacious 2 bedroom downtown very nice area!
2 bedrooms, 3 beds, 1 bathroom
19–24 Oct
4.79 out of 5 average rating, 62 reviews
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Top guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
22–27 Oct
4.92 out of 5 average rating, 330 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 Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 bathrooms
19–24 Oct
5.0 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
1–6 Oct
5.0 out of 5 average rating, 3 reviews