Search results; Over 1,000 homes in Pittsfield

Serviced apartment in Pittsfield
One Bedroom Apartment with a full kitchen
1 bedroom, 2 beds, 1 bathroom
6–11 Jul
,
4.83 out of 5 average rating, 6 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
12–17 Jul
5.0 out of 5 average rating, 14 reviews
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
12–17 Jul
4.94 out of 5 average rating, 47 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
6–11 Jul
4.95 out of 5 average rating, 214 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 25 reviews
Home in Pittsfield
Four Seasons Retreat
3 bedrooms, 6 beds, 2 bathrooms
26–31 Jul
4.75 out of 5 average rating, 32 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, 455 reviews
Room in Pittsfield
The Yellow Room
1 double bed, 1.5 bathrooms
25–30 Jul
4.84 out of 5 average rating, 85 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 80 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Jul
4.91 out of 5 average rating, 314 reviews
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Pittsfield
Elmer Estate
3 bedrooms, 3 beds, 1 bathroom
21–26 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bathroom
9–14 Dec
4.96 out of 5 average rating, 49 reviews
Guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds, 1 bathroom
4–9 Jul
4.97 out of 5 average rating, 115 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 310 reviews
Guest favourite
Home in Lenox
Cozy Home in Lenox
2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 103 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 bathrooms
8–13 Jul
5.0 out of 5 average rating, 40 reviews