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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Summer on the Lake - Berkshires near Tanglewood
3 bedrooms, 4 beds, 2 private bathrooms
13–18 Sept
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4.96 out of 5 average rating, 74 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
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, 2 bathrooms
30 Aug – 4 Sept
4.91 out of 5 average rating, 58 reviews
Superhost
Room in Pittsfield
Sunny Room in Downtown Victorian
1 bed, 2 bathrooms
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, 1 bathroom
22–27 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, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 464 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.96 out of 5 average rating, 228 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
3–8 Oct
5.0 out of 5 average rating, 91 reviews
Room in Pittsfield
The Yellow Room
1 double bed, 1.5 bathrooms
12–17 Oct
4.84 out of 5 average rating, 90 reviews
Top guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 queen bed, 1 bathroom
12–17 Sept
4.92 out of 5 average rating, 136 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
6–11 Sept
4.84 out of 5 average rating, 43 reviews
Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
4.81 out of 5 average rating, 210 reviews
Room in Pittsfield
Cozy room in Pittsfield #2
1 double bed, 1.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 202 reviews
Top guest favourite
Flat in New Lebanon
Folk Art Studio: 1-bedroom near the Berkshires
1 bedroom, 2 beds, 1 bathroom
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, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 616 reviews
Place to stay in Lenox
Private outbuilding retreat room at Eastover
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.5 out of 5 average rating, 12 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 324 reviews