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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 bed, 1 private bathroom
23–28 Aug
,
4.91 out of 5 average rating, 128 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, 18 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
23–28 Aug
4.92 out of 5 average rating, 49 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, 86 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, 27 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed
6–11 Sept
4.99 out of 5 average rating, 316 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds
23–28 Aug
4.95 out of 5 average rating, 218 reviews
Guest favourite
Home in Pittsfield
A Ray of Sunshine-Lakefront-New Construction- ski
5 bedrooms
26–31 Jul
5.0 out of 5 average rating, 35 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
9–14 Aug
4.92 out of 5 average rating, 318 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
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 41 reviews
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds
24–29 Aug
4.95 out of 5 average rating, 37 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds
20–25 Nov
4.96 out of 5 average rating, 51 reviews
Guest favourite
Home in Lenox
Cozy Home in Lenox
2 bedrooms, 2 beds
20–25 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Room in Pittsfield
Sunny Room in Downtown Victorian
1 bed
21–26 Jul
4.78 out of 5 average rating, 18 reviews
Home in New Lebanon
Berkshire Summer Retreat | Minutes to Tanglewood
4 bedrooms, 4 beds
19–24 Jul
4.76 out of 5 average rating, 17 reviews
Home in Lenox
7 Minute Walk to Tanglewood from New 2BR Home
2 bedrooms, 2 queen beds
25–30 Jul
New place to stay
Top guest favourite
Home in Hinsdale
Berkshire Lake-side Retreat
2 bedrooms, 4 beds
2–7 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Cottage in Lanesborough
Wildlife Lakeside Cottage; views/wildlife
3 bedrooms, 4 beds
23–28 Aug
4.85 out of 5 average rating, 296 reviews