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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
4–9 Oct
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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, 1 bathroom
4–9 Oct
4.65 out of 5 average rating, 52 reviews
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Top guest favourite
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
5.0 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
4–9 Oct
4.88 out of 5 average rating, 75 reviews
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Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
3–8 Oct
4.97 out of 5 average rating, 78 reviews
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Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds, 1 bathroom
21–26 Oct
4.98 out of 5 average rating, 469 reviews
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Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
25–30 Oct
4.95 out of 5 average rating, 240 reviews
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Top guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
22–27 Oct
4.92 out of 5 average rating, 330 reviews
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Guest favourite
Flat in Lenox
1BR Apt, private entry, kitchenette & fridge
1 bedroom, 3 beds, 1 bathroom
1–6 Oct
4.91 out of 5 average rating, 11 reviews
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Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
4–9 Oct
4.92 out of 5 average rating, 50 reviews
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Guest favourite
Home in Pittsfield
Dancing Horse Lodge
3 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.87 out of 5 average rating, 331 reviews
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Top guest favourite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 bedrooms, 5 beds, 2 bathrooms
13–18 Oct
4.95 out of 5 average rating, 75 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
4–9 Oct
4.98 out of 5 average rating, 85 reviews
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Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 130 reviews
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Guest favourite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 26 reviews
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Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Oct
5.0 out of 5 average rating, 27 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
19–24 Oct
5.0 out of 5 average rating, 47 reviews
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Superhost
Flat in Pittsfield
Spacious 2 bedroom downtown very nice area!
2 bedrooms, 3 beds, 1 bathroom
19–24 Oct
4.79 out of 5 average rating, 61 reviews