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Search results; Over 1,000 homes in Pittsfield

Flat in Pittsfield
One Bedroom Apartment with a full kitchen
1 bedroom, 2 beds, 1 bathroom
3–8 Sept
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4.83 out of 5 average rating, 6 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
6–11 Sept
4.64 out of 5 average rating, 50 reviews
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
6–11 Sept
4.91 out of 5 average rating, 46 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, 466 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
8–13 Sept
5.0 out of 5 average rating, 37 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
10–15 Sept
4.88 out of 5 average rating, 69 reviews
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds
6–11 Sept
New place to stay
Top guest favourite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds
5–10 Sept
4.94 out of 5 average rating, 47 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
7–12 Sept
4.86 out of 5 average rating, 51 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, 232 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds
9–14 Sept
4.97 out of 5 average rating, 74 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, 95 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, 141 reviews
Top guest favourite
Cottage in Pittsfield
Charming Lakeview Cottage in the Berkshires
1 bedroom, 2 beds
9–14 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Pittsfield
Charming Historic Retreat, <15 min from Lenox
4 bedrooms, 6 beds
10–15 Sept
5.0 out of 5 average rating, 15 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
Superhost
Home in Pittsfield
Grand Berkshire Manor By Evergreen Home
5 bedrooms, 8 beds
5–10 Sept
New place to stay
Guest favourite
Resort in Hancock
Country Inn Suite at Jiminy Peak - No fees added
1 bedroom, 2 beds
4–9 Sept
4.74 out of 5 average rating, 289 reviews
Guest favourite
Home in Dalton
Willowbrook: A Sun Filled, Mid-century Modern Home
7 bedrooms, 8 beds
20–25 Sept
4.78 out of 5 average rating, 113 reviews