filters

Search results; Over 1,000 homes in Pittsfield

Photo 1 of 28
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 private bathroom
1–6 Nov
,
4.99 out of 5 average rating, 338 reviews
Photo 1 of 29
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
4–9 Oct
4.65 out of 5 average rating, 52 reviews
Photo 1 of 21
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
25–30 Oct
5.0 out of 5 average rating, 38 reviews
Photo 1 of 29
Top guest favourite
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds
18–23 Oct
5.0 out of 5 average rating, 7 reviews
Photo 1 of 6
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
4–9 Oct
4.88 out of 5 average rating, 75 reviews
Photo 1 of 29
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds
3–8 Oct
4.97 out of 5 average rating, 78 reviews
Photo 1 of 29
Top guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
22–27 Oct
4.92 out of 5 average rating, 330 reviews
Photo 1 of 6
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
4–9 Oct
4.92 out of 5 average rating, 50 reviews
Photo 1 of 6
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds
21–26 Oct
4.98 out of 5 average rating, 469 reviews
Photo 1 of 29
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds
25–30 Oct
4.95 out of 5 average rating, 240 reviews
Photo 1 of 29
Top guest favourite
Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
6 bedrooms, 10 beds
4–9 Oct
4.98 out of 5 average rating, 85 reviews
Photo 1 of 19
Guest favourite
Home in Pittsfield
Dancing Horse Lodge
3 bedrooms, 3 beds
25–30 Oct
4.87 out of 5 average rating, 331 reviews
Photo 1 of 23
Guest favourite
Flat in Lenox
1BR Apt, private entry, kitchenette & fridge
1 bedroom, 3 beds
1–6 Oct
4.91 out of 5 average rating, 11 reviews
Photo 1 of 15
Top guest favourite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 bedrooms, 5 beds
13–18 Oct
4.95 out of 5 average rating, 75 reviews
Photo 1 of 29
Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds
4–9 Oct
4.97 out of 5 average rating, 130 reviews
Photo 1 of 23
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds
1–6 Oct
4.96 out of 5 average rating, 76 reviews
Photo 1 of 20
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds
19–24 Oct
5.0 out of 5 average rating, 47 reviews
Photo 1 of 20
Superhost
Flat in Pittsfield
Spacious 2 bedroom downtown very nice area!
2 bedrooms, 3 beds
19–24 Oct
4.79 out of 5 average rating, 61 reviews
Photo 1 of 28
Guest favourite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds
1–6 Oct
5.0 out of 5 average rating, 26 reviews