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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Berkshire Lakehouse - 3 bedrooms - sleeps 5
3 bedrooms, 3 beds, 1 private bathroom
22–27 Sept
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4.92 out of 5 average rating, 49 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds
9–14 Aug
4.96 out of 5 average rating, 226 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
30 Aug – 4 Sept
4.86 out of 5 average rating, 28 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
26–31 Oct
5.0 out of 5 average rating, 32 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
6–11 Sept
4.83 out of 5 average rating, 40 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
9–14 Aug
4.92 out of 5 average rating, 324 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
22–27 Aug
4.65 out of 5 average rating, 43 reviews
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds
23–28 Aug
4.97 out of 5 average rating, 70 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed
24–29 Sept
5.0 out of 5 average rating, 88 reviews
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds
23–28 Aug
4.98 out of 5 average rating, 464 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 312 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds
20–25 Nov
4.96 out of 5 average rating, 52 reviews
Flat in Pittsfield
Spacious Green 2 bedroom Downtown
2 bedrooms, 4 beds
23–28 Aug
4.81 out of 5 average rating, 52 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds
2–7 Sept
4.97 out of 5 average rating, 71 reviews
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds
24–29 Aug
4.95 out of 5 average rating, 38 reviews
Guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds
7–12 Sept
4.93 out of 5 average rating, 109 reviews
Room in Pittsfield
The Yellow Room
1 double bed
28 Sept – 3 Oct
4.84 out of 5 average rating, 90 reviews
Superhost
Room in Pittsfield
Cozy Corner Room in Downtown Victorian
1 bed
14–19 Sept