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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 private bathroom
28 Oct – 2 Nov
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4.99 out of 5 average rating, 334 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
10–15 Sept
4.87 out of 5 average rating, 70 reviews
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
17–22 Sept
4.91 out of 5 average rating, 47 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
8–13 Sept
4.64 out of 5 average rating, 50 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, 466 reviews
Top guest favourite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds, 4 bathrooms
9–14 Sept
4.94 out of 5 average rating, 47 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
4.95 out of 5 average rating, 234 reviews
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
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
Cottage in Pittsfield
Lake Views & Dock Access - Pittsfield Cottage!
4 bedrooms, 6 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Sept
4.96 out of 5 average rating, 76 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, 95 reviews
Top guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 bathrooms
8–13 Sept
4.95 out of 5 average rating, 42 reviews
Flat in Pittsfield
Mid-Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Sept
New place to stay
Top guest favourite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
4.95 out of 5 average rating, 75 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
Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 27 reviews
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
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, 76 reviews