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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, 3 bathrooms
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, 2 bathrooms
10–15 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, 2 bathrooms
6–11 Sept
4.85 out of 5 average rating, 48 reviews
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Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds, 1 bathroom
12–17 Sept
4.98 out of 5 average rating, 466 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, 231 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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Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.64 out of 5 average rating, 50 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
1–6 Nov
4.84 out of 5 average rating, 194 reviews
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Superhost
Home in Pittsfield
Grand Berkshire Manor By Evergreen Home
5 bedrooms, 8 beds, 4 bathrooms
3–8 Sept
New place to stay
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Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Sept
4.97 out of 5 average rating, 74 reviews
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Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 95 reviews
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Guest favourite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
3 bedrooms, 4 beds, 1 bathroom
28 Oct – 2 Nov
4.93 out of 5 average rating, 133 reviews
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Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 bathrooms
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, 1 bathroom
12–17 Sept
4.92 out of 5 average rating, 141 reviews
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Guest favourite
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
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Sept
4.97 out of 5 average rating, 75 reviews
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Top guest favourite
Home in Pittsfield
Charming Historic Retreat, <15 min from Lenox
4 bedrooms, 6 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 14 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
3–8 Sept
4.94 out of 5 average rating, 47 reviews