filters

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
,
4.99 out of 5 average rating, 326 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
30 Aug – 4 Sept
4.88 out of 5 average rating, 32 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, 58 reviews
Superhost
Room in Pittsfield
Sunny Room in Downtown Victorian
1 bed
17–22 Aug
4.71 out of 5 average rating, 21 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
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed
3–8 Oct
5.0 out of 5 average rating, 91 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
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds
23–28 Aug
4.96 out of 5 average rating, 228 reviews
Top guest favourite
Flat in New Lebanon
Folk Art Studio: 1-bedroom near the Berkshires
1 bedroom, 2 beds
4–9 Sept
5.0 out of 5 average rating, 31 reviews
Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
2 bedrooms, 3 beds
8–13 Sept
4.81 out of 5 average rating, 210 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed
30 Aug – 4 Sept
4.97 out of 5 average rating, 617 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, 33 reviews
Top guest favourite
Cottage in New Lebanon
The Writer's Cottage
2 bedrooms, 2 beds
19–24 Aug
4.94 out of 5 average rating, 214 reviews
Home in Lenox
The Gardener's Cottage 1893 at Ventfort Hall
2 bedrooms, 2 queen beds
22–27 Aug
New place to stay
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
6–11 Sept
4.84 out of 5 average rating, 44 reviews
Guest favourite
Room in Becket
East b.r. in upstairs suite of open plan home
23–28 Aug
4.87 out of 5 average rating, 261 reviews
Top guest favourite
Flat in North Adams
Steps to MoCA: 2bd + SAUNA!
2 bedrooms, 3 beds
13–18 Sept
4.96 out of 5 average rating, 724 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
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 queen bed
12–17 Sept
4.92 out of 5 average rating, 136 reviews