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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
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4.99 out of 5 average rating, 311 reviews
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
5.0 out of 5 average rating, 16 reviews, 2 beds, 3 bathrooms
12–17 Jul
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
5.0 out of 5 average rating, 4 reviews, 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
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
4.95 out of 5 average rating, 215 reviews, 3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
Guest favourite
Flat in Pittsfield
Marie's Place
4.91 out of 5 average rating, 315 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
4.98 out of 5 average rating, 456 reviews, 2 beds, 1 bathroom
23–28 Aug
Home in Lanesborough
Casa Demeo, Private Berkshire Retreat
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 3 bathrooms
6–11 Jul
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
4.92 out of 5 average rating, 48 reviews, 1 bed, 2 bathrooms
23–28 Aug
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 Hinsdale
Berkshire Lake-side Retreat
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 4 beds, 2 bathrooms
8–13 Jul
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
5.0 out of 5 average rating, 83 reviews, 1 queen bed, 1 bathroom
24–29 Aug
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
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
4.77 out of 5 average rating, 31 reviews, 1 bed, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
4.97 out of 5 average rating, 63 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, 104 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
5.0 out of 5 average rating, 41 reviews, 4 bedrooms, 4 beds, 1.5 bathrooms
8–13 Jul
Top guest favourite
Home in Pittsfield
Friendly Hills | Passive Home • EV Charger
4.94 out of 5 average rating, 33 reviews, 3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
4.97 out of 5 average rating, 67 reviews, 2 bedrooms, 2 beds, 1 bathroom
5–10 Nov