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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
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4.95 out of 5 average rating, 217 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed
24–29 Aug
5.0 out of 5 average rating, 85 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
23–28 Aug
4.92 out of 5 average rating, 48 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
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds
22–27 Aug
4.98 out of 5 average rating, 457 reviews
Room in Pittsfield
The Yellow Room
1 double bed
12–17 Jul
4.84 out of 5 average rating, 87 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed
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
28 Jul – 2 Aug
4.93 out of 5 average rating, 105 reviews
Guest favourite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
3 bedrooms, 4 beds
28 Oct – 2 Nov
4.93 out of 5 average rating, 133 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds
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
23–28 Aug
4.96 out of 5 average rating, 199 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
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
23–28 Aug
4.91 out of 5 average rating, 126 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds
10–15 Jul
5.0 out of 5 average rating, 41 reviews
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds
12–17 Jul
5.0 out of 5 average rating, 11 reviews
Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
2 bedrooms, 3 beds
25–30 Jul
4.82 out of 5 average rating, 207 reviews
Top guest favourite
Room in Pittsfield
Creative Haven in the Berkshires - Nest Room
1 queen bed
22–27 Aug
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Pittsfield
Relaxing Berkshire getaway
2 bedrooms, 3 beds
26–31 Jul
4.97 out of 5 average rating, 73 reviews