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Search results; Over 1,000 homes in Pittsfield

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Guest favourite
Home in Pittsfield
Hidden Oasis in the Mountains by Evergreen Home
5 bedrooms, 8 beds, 3 private bathrooms
19–24 Sept
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4.97 out of 5 average rating, 157 reviews
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Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
20–25 Sept
4.65 out of 5 average rating, 51 reviews
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Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
25–30 Oct
5.0 out of 5 average rating, 37 reviews
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Top guest favourite
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds
19–24 Sept
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds
21–26 Oct
4.98 out of 5 average rating, 469 reviews
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Top guest favourite
Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
6 bedrooms, 10 beds
26 Sept – 1 Oct
4.98 out of 5 average rating, 85 reviews
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Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
20–25 Sept
4.88 out of 5 average rating, 74 reviews
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Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
21–26 Sept
4.92 out of 5 average rating, 48 reviews
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Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 238 reviews
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Flat in Pittsfield
Mid-Berkshires
2 bedrooms, 2 queen beds
20–25 Sept
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
20–25 Sept
4.85 out of 5 average rating, 54 reviews
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Top guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
27 Sept – 2 Oct
4.92 out of 5 average rating, 329 reviews
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Top guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 queen bed
20–25 Sept
4.92 out of 5 average rating, 144 reviews
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Top guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds
22–27 Oct
4.93 out of 5 average rating, 117 reviews
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Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds
18–23 Sept
4.97 out of 5 average rating, 78 reviews
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Top guest favourite
Home in Pittsfield
Charming Historic Retreat, <15 min from Lenox
4 bedrooms, 6 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds
20–25 Sept
4.94 out of 5 average rating, 47 reviews
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Guest favourite
Flat in Pittsfield
Spacious 2 bedroom downtown very nice area!
2 bedrooms, 3 beds
20–25 Sept
4.78 out of 5 average rating, 60 reviews
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Home in Pittsfield
Cozy escape to the Berkshires
2 bedrooms, 2 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews