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
2 beds
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
6–11 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
Top guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
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
6–11 Jul
4.95 out of 5 average rating, 214 reviews
Home in Pittsfield
Four Seasons Retreat
3 bedrooms, 6 beds
26–31 Jul
4.75 out of 5 average rating, 32 reviews
Room in Pittsfield
The Yellow Room
1 double bed
25–30 Jul
4.84 out of 5 average rating, 85 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
27 Aug – 1 Sept
5.0 out of 5 average rating, 25 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
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds
8–13 Jul
5.0 out of 5 average rating, 40 reviews
Guest favourite
Home in Pittsfield
Berkshire Getaway Ranch 3 acres + saltwater pool
2 bedrooms, 3 beds
6–11 Jul
4.92 out of 5 average rating, 103 reviews
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds
23–28 Aug
4.98 out of 5 average rating, 455 reviews
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds
22–27 Aug
4.97 out of 5 average rating, 60 reviews
Guest favourite
Flat in Pittsfield
Berkshire’s Sweet Spot- Pool and Spa- Discount Now
3 bedrooms, 4 beds
4–9 Jul
4.93 out of 5 average rating, 83 reviews
Guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds
4–9 Jul
4.97 out of 5 average rating, 115 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
6–11 Jul
4.91 out of 5 average rating, 314 reviews
Top guest favourite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 bedrooms, 5 beds
30 Aug – 4 Sept
4.95 out of 5 average rating, 74 reviews
Guest favourite
Home in Lenox
Cozy Home in Lenox
2 bedrooms, 2 beds
6–11 Jul
5.0 out of 5 average rating, 7 reviews