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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Dancing Horse Lodge
3 bedrooms, 3 beds, 1 private bathroom
11–16 Sept
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4.87 out of 5 average rating, 330 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
17–22 Sept
4.87 out of 5 average rating, 70 reviews
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds
12–17 Sept
4.98 out of 5 average rating, 469 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
20–25 Sept
5.0 out of 5 average rating, 37 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
10–15 Sept
4.64 out of 5 average rating, 50 reviews
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds
14–19 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds
11–16 Sept
4.95 out of 5 average rating, 236 reviews
Top guest favourite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds
12–17 Sept
4.94 out of 5 average rating, 47 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed
18–23 Oct
5.0 out of 5 average rating, 99 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds
10–15 Sept
4.96 out of 5 average rating, 76 reviews
Top guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 queen bed
12–17 Sept
4.92 out of 5 average rating, 143 reviews
Guest favourite
Cottage in Pittsfield
Lake Views & Dock Access - Pittsfield Cottage!
4 bedrooms, 6 beds
10–15 Sept
5.0 out of 5 average rating, 9 reviews
Flat in Pittsfield
Mid-Berkshires
2 bedrooms, 2 queen beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Pittsfield
Berkshire Lakehouse - 3 bedrooms - sleeps 5
3 bedrooms, 3 beds
22–27 Sept
4.92 out of 5 average rating, 50 reviews
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
18–23 Sept
4.91 out of 5 average rating, 47 reviews
Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 bedrooms, 2 beds
1–6 Nov
4.84 out of 5 average rating, 194 reviews
Top guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds
10–15 Sept
4.95 out of 5 average rating, 42 reviews
Top guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
16–21 Sept
4.92 out of 5 average rating, 329 reviews
Guest favourite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
3 bedrooms, 4 beds
28 Oct – 2 Nov
4.93 out of 5 average rating, 135 reviews