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Search results; Over 1,000 homes in Pittsfield

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Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
1 bedroom, 2 beds, 1 private bathroom
12–17 Sept
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4.98 out of 5 average rating, 466 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
4.89 out of 5 average rating, 38 reviews
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Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
7–12 Sept
4.9 out of 5 average rating, 60 reviews
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Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 37 reviews
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Superhost
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
4.96 out of 5 average rating, 230 reviews
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Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
6–11 Sept
4.84 out of 5 average rating, 45 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
8–13 Sept
5.0 out of 5 average rating, 44 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
26 Sept – 1 Oct
4.98 out of 5 average rating, 83 reviews
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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
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 114 reviews
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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, 73 reviews
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Guest favourite
Home in Pittsfield
Dancing Horse Lodge
3 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.87 out of 5 average rating, 330 reviews
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Superhost
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
4.92 out of 5 average rating, 327 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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Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 74 reviews
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Guest favourite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 25 reviews
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Top guest favourite
Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 26 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, 139 reviews
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Home in Pittsfield
Lake House Onota Lake
3 bedrooms, 6 beds, 2 bathrooms
3–8 Sept