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
23–28 Aug
,
4.99 out of 5 average rating, 310 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
12–17 Jul
5.0 out of 5 average rating, 14 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
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed
24–29 Aug
5.0 out of 5 average rating, 82 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
5–10 Jul
4.64 out of 5 average rating, 28 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, 456 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
5–10 Jul
4.77 out of 5 average rating, 30 reviews
Top guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
23–28 Aug
4.94 out of 5 average rating, 47 reviews
Room in Pittsfield
The Yellow Room
1 double bed
27 Jul – 1 Aug
4.84 out of 5 average rating, 85 reviews
Guest favourite
Home in Pittsfield
Elmer Estate
3 bedrooms, 3 beds
21–26 Oct
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds
12–17 Jul
4.94 out of 5 average rating, 35 reviews
Guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 queen bed
23–28 Aug
4.92 out of 5 average rating, 120 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds
9–14 Dec
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds
7–12 Sept
4.93 out of 5 average rating, 104 reviews
Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
2 bedrooms, 3 beds
6–11 Jul
4.82 out of 5 average rating, 207 reviews
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
2 bedrooms, 2 queen beds
23–28 Aug
4.96 out of 5 average rating, 197 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds
5–10 Nov
4.97 out of 5 average rating, 66 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds
6–11 Jul
4.95 out of 5 average rating, 214 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
6–11 Jul
4.91 out of 5 average rating, 315 reviews