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
23–28 Aug
,
4.99 out of 5 average rating, 310 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
5.0 out of 5 average rating, 14 reviews, 2 beds, 3 bathrooms
12–17 Jul
Top guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
4.94 out of 5 average rating, 47 reviews, 1 bed, 2 bathrooms
12–17 Jul
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
5.0 out of 5 average rating, 25 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
4.98 out of 5 average rating, 455 reviews, 2 beds, 1 bathroom
23–28 Aug
Flat in Pittsfield
Petite Paris
4.81 out of 5 average rating, 37 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
5–10 Jul
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
5.0 out of 5 average rating, 80 reviews, 1 queen bed, 1 bathroom
19–24 Jul
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
4.95 out of 5 average rating, 214 reviews, 3 bedrooms, 5 beds, 2 bathrooms
6–11 Jul
Guest favourite
Home in Lenox
Cozy Home in Lenox
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4.99 out of 5 average rating, 308 reviews, 3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
Room in Pittsfield
The Yellow Room
4.84 out of 5 average rating, 85 reviews, 1 double bed, 1.5 bathrooms
25–30 Jul
Home in Pittsfield
Four Seasons Retreat
4.75 out of 5 average rating, 32 reviews, 3 bedrooms, 6 beds, 2 bathrooms
26–31 Jul
Guest favourite
Flat in Pittsfield
Beautiful & Serene Getaway
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 2 beds, 1 bathroom
5–10 Jul
Guest favourite
Flat in Pittsfield
Marie's Place
4.91 out of 5 average rating, 314 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Home in Lanesborough
The Pond House
4.96 out of 5 average rating, 49 reviews, 3 bedrooms, 4 beds, 1 bathroom
9–14 Dec
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
4.97 out of 5 average rating, 60 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
22–27 Aug
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
4.93 out of 5 average rating, 103 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept