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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 private bathroom
8–13 Sept
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5.0 out of 5 average rating, 37 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
6–11 Sept
4.91 out of 5 average rating, 46 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
6–11 Sept
4.86 out of 5 average rating, 51 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.64 out of 5 average rating, 50 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
10–15 Sept
4.9 out of 5 average rating, 68 reviews
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
13–18 Sept
New place to stay
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
3–8 Sept
4.94 out of 5 average rating, 47 reviews
Top 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, 232 reviews
Superhost
Home in Pittsfield
Grand Berkshire Manor By Evergreen Home
5 bedrooms, 8 beds, 4 bathrooms
3–8 Sept
New place to stay
Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
4.84 out of 5 average rating, 194 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 95 reviews
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, 74 reviews
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, 141 reviews
Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 bathrooms
2–7 Sept
5.0 out of 5 average rating, 20 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
Guest favourite
Resort in Hancock
Country Inn Suite at Jiminy Peak - No fees added
1 bedroom, 2 beds, 1 bathroom
2–7 Sept
4.74 out of 5 average rating, 289 reviews
Guest favourite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
3 bedrooms, 4 beds, 1 bathroom
28 Oct – 2 Nov
4.93 out of 5 average rating, 133 reviews
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, 45 reviews