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Search results; Over 1,000 homes in Pittsfield

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Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 private bathroom
8–13 Sept
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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
6–11 Sept
4.9 out of 5 average rating, 40 reviews
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Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
7–12 Sept
4.9 out of 5 average rating, 63 reviews
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Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
6–11 Sept
4.85 out of 5 average rating, 47 reviews
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Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
7–12 Sept
4.63 out of 5 average rating, 49 reviews
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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
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Superhost
Home in Pittsfield
Grand Berkshire Manor By Evergreen Home
5 bedrooms, 8 beds
2–7 Sept
New place to stay
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Home in Pittsfield
Lake House Onota Lake
3 bedrooms, 6 beds
6–11 Sept
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Top guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds
11–16 Sept
4.96 out of 5 average rating, 230 reviews
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Top guest favourite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds
1–6 Sept
4.94 out of 5 average rating, 47 reviews
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Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed
3–8 Oct
5.0 out of 5 average rating, 94 reviews
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Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds
9–14 Sept
4.97 out of 5 average rating, 74 reviews
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Guest favourite
Resort in Hancock
Country Inn Suite at Jiminy Peak - No fees added
1 bedroom, 2 beds
1–6 Sept
4.74 out of 5 average rating, 289 reviews
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Guest favourite
Home in Pittsfield
Berkshire Views
6 bedrooms, 7 beds
13–18 Sept
5.0 out of 5 average rating, 19 reviews
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Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
6–11 Sept
4.92 out of 5 average rating, 328 reviews
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Room in Pittsfield
The Yellow Room
1 double bed
12–17 Oct
4.83 out of 5 average rating, 95 reviews
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Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds
1–6 Sept
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 queen bed
12–17 Sept
4.92 out of 5 average rating, 140 reviews
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Guest favourite
Home in Dalton
Willowbrook: A Sun Filled, Mid-century Modern Home
7 bedrooms, 8 beds
20–25 Sept
4.78 out of 5 average rating, 113 reviews