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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 beds, 1 shared bathroom
9–14 Aug
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4.92 out of 5 average rating, 322 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
4.96 out of 5 average rating, 225 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
30 Aug – 4 Sept
4.86 out of 5 average rating, 28 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 32 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
6–11 Sept
4.83 out of 5 average rating, 40 reviews
Guest favourite
Farm stay in New Lebanon
NEW RENO - Chalet-style farm loft near Tanglewood
1 bedroom, 3 beds, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 70 reviews
Guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 122 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 312 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
22–27 Aug
4.65 out of 5 average rating, 43 reviews
Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
4.84 out of 5 average rating, 194 reviews
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
23–28 Aug
4.97 out of 5 average rating, 70 reviews
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
4.95 out of 5 average rating, 38 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bathroom
20–25 Nov
4.96 out of 5 average rating, 52 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
24–29 Sept
5.0 out of 5 average rating, 88 reviews
Superhost
Room in Pittsfield
Cozy Corner Room in Downtown Victorian
1 bed, 2.5 bathrooms
14–19 Sept
Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 bathroom
25–30 Sept
4.99 out of 5 average rating, 325 reviews
Guest favourite
Resort in Hancock
Country Inn Suite at Jiminy Peak - No fees added
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
4.73 out of 5 average rating, 271 reviews