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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
25–30 Sept
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4.99 out of 5 average rating, 323 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, 225 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
23–28 Aug
4.83 out of 5 average rating, 40 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
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
9–14 Aug
4.92 out of 5 average rating, 322 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
Room in Pittsfield
The Yellow Room
1 double bed
29 Aug – 3 Sept
4.84 out of 5 average rating, 90 reviews
Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds
9–14 Aug
4.97 out of 5 average rating, 122 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
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
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 bedrooms, 2 beds
1–6 Nov
4.84 out of 5 average rating, 194 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
30 Aug – 4 Sept
4.91 out of 5 average rating, 56 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
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
Guest favourite
Resort in Hancock
Country Inn Suite at Jiminy Peak - No fees added
1 bedroom, 2 beds
9–14 Aug
4.73 out of 5 average rating, 270 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
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed
13–18 Sept
5.0 out of 5 average rating, 87 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