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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Hidden Oasis in the Mountains by Evergreen Home
5 bedrooms, 8 beds, 3 private bathrooms
19–24 Sept
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4.97 out of 5 average rating, 155 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds
23–28 Aug
4.96 out of 5 average rating, 228 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
22–27 Aug
4.65 out of 5 average rating, 43 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
26–31 Oct
5.0 out of 5 average rating, 32 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
23–28 Aug
4.92 out of 5 average rating, 324 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
30 Aug – 4 Sept
4.86 out of 5 average rating, 28 reviews
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds
23–28 Aug
4.97 out of 5 average rating, 71 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
6–11 Sept
4.83 out of 5 average rating, 40 reviews
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds
23–28 Aug
4.98 out of 5 average rating, 464 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
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed
3–8 Oct
5.0 out of 5 average rating, 88 reviews
Home in Lenox
Lenox cottage 1 mile from town center 2 bed 2 bath
2 bedrooms, 2 beds
28 Aug – 2 Sept
New place to stay
Guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds
7–12 Sept
4.93 out of 5 average rating, 110 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 313 reviews
Home in Pittsfield
3 Acres, Mtn Views, Hot Tub, Steps to Winery
3 bedrooms, 3 beds
9–14 Sept
New place to stay
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds
2–7 Sept
4.97 out of 5 average rating, 71 reviews
Superhost
Room in Pittsfield
Sunny Room in Downtown Victorian
1 bed
17–22 Aug
4.75 out of 5 average rating, 20 reviews
Guest favourite
Guest suite in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
1 bedroom, 2 beds
16–21 Aug
4.81 out of 5 average rating, 95 reviews