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
5.0 out of 5 average rating, 14 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, 3 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
4.64 out of 5 average rating, 28 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Jul
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
4.77 out of 5 average rating, 30 reviews, 1 bed, 2 bathrooms
5–10 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, 214 reviews, 3 bedrooms, 5 beds, 2 bathrooms
6–11 Jul
Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
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
Top guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
4.94 out of 5 average rating, 47 reviews, 1 bed, 2 bathrooms
23–28 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
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
Flat in Pittsfield
Marie's Place, Unit 1
4.97 out of 5 average rating, 115 reviews, 3 bedrooms, 3 beds, 1 bathroom
4–9 Jul
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
4.97 out of 5 average rating, 66 reviews, 2 bedrooms, 2 beds, 1 bathroom
5–10 Nov
Guest favourite
Home in Pittsfield
Elmer Estate
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 3 beds, 1 bathroom
21–26 Oct
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
4.99 out of 5 average rating, 310 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Home in New Lebanon
Above the Clouds Mountain Retreat
New place to stay, 3 bedrooms, 3 beds, 4 bathrooms
14–19 Jul
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 Pittsfield
Marie’s Place unit 3
4.97 out of 5 average rating, 62 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
22–27 Aug