filters

Search results; Over 1,000 homes in Pittsfield

Photo 1 of 21
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 private bathroom
25–30 Oct
,
5.0 out of 5 average rating, 37 reviews
Photo 1 of 29
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, 85 reviews
Photo 1 of 6
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
21–26 Sept
4.92 out of 5 average rating, 48 reviews
Photo 1 of 29
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 238 reviews
Photo 1 of 6
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds, 1 bathroom
17–22 Sept
4.98 out of 5 average rating, 469 reviews
Photo 1 of 29
Top guest favourite
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 6 reviews
Photo 1 of 6
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
20–25 Sept
4.88 out of 5 average rating, 74 reviews
Photo 1 of 22
Top guest favourite
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
Photo 1 of 15
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
Photo 1 of 29
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.65 out of 5 average rating, 51 reviews
Photo 1 of 6
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
20–25 Sept
4.85 out of 5 average rating, 54 reviews
Photo 1 of 29
Top guest favourite
Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
3 bedrooms, 4 beds, 2.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 26 reviews
Photo 1 of 29
Guest favourite
Home in Pittsfield
Berkshire Estate
9 bedrooms, 10 beds, 4.5 bathrooms
17–22 Sept
4.86 out of 5 average rating, 22 reviews
Photo 1 of 29
Top guest favourite
Home in Pittsfield
Charming Historic Retreat, <15 min from Lenox
4 bedrooms, 6 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 15 reviews
Photo 1 of 29
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
18–23 Sept
4.97 out of 5 average rating, 78 reviews
Photo 1 of 21
Guest favourite
Home in Pittsfield
Berkshire Lakehouse - 3 bedrooms - sleeps 5
3 bedrooms, 3 beds, 1 bathroom
22–27 Sept
4.92 out of 5 average rating, 50 reviews
Photo 1 of 23
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
21–26 Sept
4.96 out of 5 average rating, 76 reviews
Photo 1 of 29
Guest favourite
Home in Pittsfield
Hidden Oasis in the Mountains by Evergreen Home
5 bedrooms, 8 beds, 3 bathrooms
19–24 Sept
4.97 out of 5 average rating, 157 reviews
Photo 1 of 20
Flat in Pittsfield
Mid-Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 4 reviews