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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds, 1 private bathroom
7–12 Sept
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4.93 out of 5 average rating, 113 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
6–11 Sept
4.89 out of 5 average rating, 38 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 36 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
7–12 Sept
4.84 out of 5 average rating, 45 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
4.96 out of 5 average rating, 230 reviews
Top guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
6–11 Sept
4.92 out of 5 average rating, 59 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
4.92 out of 5 average rating, 325 reviews
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 464 reviews
Superhost
Home in Pittsfield
Grand Berkshire Manor By Evergreen Home
5 bedrooms, 8 beds, 4.5 bathrooms
2–7 Sept
New place to stay
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.66 out of 5 average rating, 47 reviews
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 73 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Sept
4.97 out of 5 average rating, 72 reviews
Guest favourite
Home in Lenox
The Gardener's Cottage 1893 at Ventfort Hall
2 bedrooms, 2 queen beds, 1.5 bathrooms
7–12 Sept
4.8 out of 5 average rating, 5 reviews
Home in Lenox
Lenox cottage 1 mile from town center 2 bed 2 bath
2 bedrooms, 2 beds, 1 bathroom
11–16 Sept
New place to stay
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 bathrooms
1–6 Sept
4.95 out of 5 average rating, 38 reviews
Guest favourite
Flat in Lenox
1BR Apt, private entry, kitchenette & fridge
1 bedroom, 3 beds, 1 bathroom
7–12 Sept
4.8 out of 5 average rating, 5 reviews
Guest favourite
Home in Pittsfield
Berkshire Lakehouse - 3 bedrooms - sleeps 5
3 bedrooms, 3 beds, 1 bathroom
22–27 Sept
4.92 out of 5 average rating, 50 reviews
Top guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 queen bed, 1 bathroom
12–17 Sept
4.92 out of 5 average rating, 138 reviews
Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
4.84 out of 5 average rating, 194 reviews