filters

Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 private bathrooms
23–28 Aug
,
4.95 out of 5 average rating, 217 reviews
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
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 48 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 83 reviews
Room in Pittsfield
The Yellow Room
1 double bed, 1.5 bathrooms
27 Jul – 1 Aug
4.84 out of 5 average rating, 87 reviews
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 457 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
12–17 Jul
4.65 out of 5 average rating, 34 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 314 reviews
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
4.93 out of 5 average rating, 105 reviews
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
4.94 out of 5 average rating, 35 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
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 316 reviews
Guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 124 reviews
Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
2 bedrooms, 3 beds, 1 bathroom
25–30 Jul
4.82 out of 5 average rating, 207 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bathroom
9–14 Dec
4.96 out of 5 average rating, 50 reviews
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 199 reviews
Place to stay in Pittsfield
Cozy room in Pittsfield #2
1 bedroom, 1 double bed, 1.5 bathrooms
11–16 Jul
Guest favourite
Home in Pittsfield
Elmer Estate
3 bedrooms, 3 beds, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 7 reviews