Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Room in Pittsfield
Stay with Rachel
Cute Room with Bay Window in Downtown Victorian
26–31 Jul
5.0 out of 5 average rating, 18 reviews
Guest favourite
Room in Pittsfield
Stay with Rachel
Romantic King Room in Downtown Victorian
23–28 Aug
4.92 out of 5 average rating, 49 reviews
Top guest favourite
Room in Pittsfield
Stay with Eileen
2-Rm Suite in the Berkshires - private BR and Den
24–29 Aug
5.0 out of 5 average rating, 86 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 beds
27 Aug – 1 Sept
5.0 out of 5 average rating, 26 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
2 beds
19–24 Jul
4.66 out of 5 average rating, 35 reviews
Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 beds
19–24 Jul
4.97 out of 5 average rating, 118 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
5 beds
26–31 Jul
4.95 out of 5 average rating, 218 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 queen beds
9–14 Aug
4.91 out of 5 average rating, 317 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4 beds
20–25 Sept
4.99 out of 5 average rating, 311 reviews
Guest favourite
Cottage in Lanesborough
Wildlife Lakeside Cottage; views/wildlife
4 beds
23–28 Aug
4.85 out of 5 average rating, 296 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bed
6–11 Sept
4.99 out of 5 average rating, 315 reviews
Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 beds
1–6 Nov
4.84 out of 5 average rating, 194 reviews
Room in Pittsfield
Stay with Susan
The Yellow Room
26–31 Aug
4.84 out of 5 average rating, 87 reviews
Top guest favourite
Room in Pittsfield
Stay with Josie
Large guest suite w/private bath in the Berkshires
23–28 Aug
4.98 out of 5 average rating, 460 reviews
Guest favourite
Home in Lenox
Cozy Home in Lenox
2 beds
16–21 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Hinsdale
Berkshire Lake-side Retreat
4 beds
2–7 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Room in Pittsfield
Stay with Rachel
Blue Suite in Downtown Victorian
23–28 Aug
4.78 out of 5 average rating, 32 reviews
Guest favourite
Room in Pittsfield
Stay with Rachel
Sunny Room in Downtown Victorian
21–26 Jul
4.78 out of 5 average rating, 18 reviews