filters

Search results; Over 1,000 homes in Pittsfield

Photo 1 of 29
Top guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 private bathrooms
4–9 Oct
,
4.95 out of 5 average rating, 43 reviews
Photo 1 of 29
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
2 beds
4–9 Oct
4.65 out of 5 average rating, 52 reviews
Photo 1 of 6
Guest favourite
Room in Pittsfield
Stay with Rachel
Romantic King Room in Downtown Victorian
4–9 Oct
4.88 out of 5 average rating, 75 reviews
Photo 1 of 6
Top guest favourite
Room in Pittsfield
Stay with Rachel
Cute Room with Bay Window in Downtown Victorian
4–9 Oct
4.92 out of 5 average rating, 50 reviews
Photo 1 of 6
Top guest favourite
Room in Pittsfield
Stay with Josie
Large guest suite w/private bath in the Berkshires
21–26 Oct
4.98 out of 5 average rating, 470 reviews
Photo 1 of 29
Top guest favourite
Home in Pittsfield
Cozy Lake Cottage
2 beds
18–23 Oct
5.0 out of 5 average rating, 7 reviews
Photo 1 of 21
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 beds
25–30 Oct
5.0 out of 5 average rating, 38 reviews
Photo 1 of 29
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
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
10 beds
4–9 Oct
4.98 out of 5 average rating, 85 reviews
Photo 1 of 15
Top guest favourite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
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
2 queen beds
22–27 Oct
4.92 out of 5 average rating, 330 reviews
Photo 1 of 20
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 beds
19–24 Oct
5.0 out of 5 average rating, 47 reviews
Photo 1 of 6
Guest favourite
Room in Pittsfield
Stay with Rachel
Blue Suite in Downtown Victorian
16–21 Oct
4.86 out of 5 average rating, 56 reviews
Photo 1 of 29
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 beds
3–8 Oct
4.97 out of 5 average rating, 78 reviews
Photo 1 of 21
Guest favourite
Home in Pittsfield
Berkshire Lakehouse - 3 bedrooms - sleeps 5
3 beds
25–30 Oct
4.92 out of 5 average rating, 50 reviews
Photo 1 of 20
Guest favourite
Flat in Pittsfield
Spacious 2 bedroom downtown very nice area!
3 beds
19–24 Oct
4.79 out of 5 average rating, 62 reviews
Photo 1 of 6
Superhost
Room in Pittsfield
Stay with Rachel
Sunny Room in Downtown Victorian
4–9 Oct
4.69 out of 5 average rating, 26 reviews
Photo 1 of 15
Home in Pittsfield
Cozy escape to the Berkshires
2 beds
1–6 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Guest favourite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
4 beds
27 Oct – 1 Nov
4.93 out of 5 average rating, 136 reviews