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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
1 bedroom, 2 beds, 1 private bathroom
23–28 Aug
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4.98 out of 5 average rating, 454 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
12–17 Jul
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
12–17 Jul
4.93 out of 5 average rating, 46 reviews
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
2 bedrooms, 2 beds
5–10 Jul
New place to stay
Flat in Pittsfield
Petite Paris
3 bedrooms, 3 beds
5–10 Jul
4.81 out of 5 average rating, 37 reviews
Home in Pittsfield
Four Seasons Retreat
3 bedrooms, 6 beds
6–11 Jul
4.74 out of 5 average rating, 31 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
1–6 Jul
4.65 out of 5 average rating, 26 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
7–12 Jul
5.0 out of 5 average rating, 24 reviews
Room in Pittsfield
The Yellow Room
1 double bed
25–30 Jul
4.84 out of 5 average rating, 85 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds
6–11 Jul
4.95 out of 5 average rating, 213 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
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
1–6 Aug
4.77 out of 5 average rating, 30 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed
19–24 Jul
5.0 out of 5 average rating, 80 reviews
Top guest favourite
Home in Pittsfield
Elmer Estate
3 bedrooms, 3 beds
22–27 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
6–11 Jul
4.92 out of 5 average rating, 311 reviews
Guest favourite
Home in Pittsfield
Berkshire Getaway Ranch 3 acres + saltwater pool
2 bedrooms, 3 beds
1–6 Jul
4.92 out of 5 average rating, 102 reviews
Home in New Lebanon
Above the Clouds Mountain Retreat
3 bedrooms, 3 beds
6–11 Jul
New place to stay
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds
5–10 Jul
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 307 reviews