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Search results; Over 1,000 homes in Pittsfield

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Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 private bathrooms
12–17 Sept
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4.95 out of 5 average rating, 237 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
17–22 Sept
4.87 out of 5 average rating, 70 reviews
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, 469 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
12–17 Sept
4.65 out of 5 average rating, 51 reviews
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Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 37 reviews
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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, 46 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 99 reviews
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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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Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 26 reviews
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Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Sept
4.96 out of 5 average rating, 76 reviews
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Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 43 reviews
Guest favourite
Cottage in Pittsfield
Lake Views & Dock Access - Pittsfield Cottage!
4 bedrooms, 6 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Dalton
Willowbrook: A Sun Filled, Mid-century Modern Home
7 bedrooms, 8 beds, 4.5 bathrooms
20–25 Sept
4.78 out of 5 average rating, 113 reviews
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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, 77 reviews
Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 27 reviews
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Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
18–23 Sept
4.91 out of 5 average rating, 47 reviews
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Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds, 4 bathrooms
20–25 Sept
4.94 out of 5 average rating, 47 reviews
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Home in Pittsfield
Charming Historic Retreat, <15 min from Lenox
4 bedrooms, 6 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Pittsfield
The Reel Retreat | Theatre & Firepit • Game Room
4 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 18 reviews