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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 bed, 1 private bathroom
12–17 Sept
,
4.92 out of 5 average rating, 137 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
6–11 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
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
24–29 Aug
4.65 out of 5 average rating, 43 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
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
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
6–11 Sept
4.84 out of 5 average rating, 44 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
Rooms in Pittsfield
Equestrian retreat
2 bedrooms, 2 queen beds
23–28 Aug
4.97 out of 5 average rating, 202 reviews
Top guest favourite
Cottage in New Lebanon
The Writer's Cottage
2 bedrooms, 2 beds
10–15 Sept
4.94 out of 5 average rating, 214 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
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, 618 reviews
Room in Pittsfield
The Yellow Room
1 double bed
12–17 Oct
4.82 out of 5 average rating, 91 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
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
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed
23–28 Aug
4.9 out of 5 average rating, 72 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds
20–25 Nov
4.96 out of 5 average rating, 53 reviews