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Search results; Over 1,000 homes in Pittsfield

Descriptions are based on details hosts provide
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 private bathroom
6–11 Sept
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4.99 out of 5 average rating, 315 reviews
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
5.0 out of 5 average rating, 17 reviews, 2 beds, 3 bathrooms
26–31 Jul
Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
4.84 out of 5 average rating, 194 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
5.0 out of 5 average rating, 86 reviews, 1 queen bed, 1 bathroom
24–29 Aug
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
4.92 out of 5 average rating, 48 reviews, 1 bed, 2 bathrooms
23–28 Aug
Top guest favourite
Room in Pittsfield
Spacious suite with homemade breakfast included
4.98 out of 5 average rating, 460 reviews, 2 beds, 1 bathroom
23–28 Aug
Room in Pittsfield
The Yellow Room
4.84 out of 5 average rating, 87 reviews, 1 double bed, 1.5 bathrooms
26–31 Aug
Guest favourite
Guest suite in Pittsfield
Tranquil annex with a fire pit
4.91 out of 5 average rating, 127 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
4.97 out of 5 average rating, 68 reviews, 2 bedrooms, 2 beds, 1 bathroom
5–10 Nov
Top guest favourite
Flat in Pittsfield
Quiet Berkshires base near ski and trails
4.93 out of 5 average rating, 105 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
Top guest favourite
Home in Lanesborough
Cabin-in-the-woods feel on a pond
4.96 out of 5 average rating, 51 reviews, 3 bedrooms, 4 beds, 1 bathroom
9–14 Dec
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
4.94 out of 5 average rating, 36 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
4.77 out of 5 average rating, 31 reviews, 1 bed, 2 bathrooms
23–28 Aug
Guest favourite
Home in Pittsfield
Solar home with heated floors and porch
4.93 out of 5 average rating, 133 reviews, 3 bedrooms, 4 beds, 1 bathroom
28 Oct – 2 Nov
Guest favourite
Home in Dalton
Willowbrook: A Sun Filled, Mid-century Modern Home
4.77 out of 5 average rating, 108 reviews, 7 bedrooms, 8 beds, 4.5 bathrooms
19–24 Jul
Guest favourite
Townhouse in Hancock
Ski-in/ski-out with pool and hot tub
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
Guest favourite
Flat in Pittsfield
Newly renovated, minutes from ski and downtown
4.91 out of 5 average rating, 317 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Guest favourite
Resort in Hancock
Ski resort suite in the Berkshires
4.72 out of 5 average rating, 267 reviews, 1 bedroom, 2 beds, 1 bathroom
15–20 Jul
Guest favourite
Home in Pittsfield
Berkshire Estate
4.81 out of 5 average rating, 16 reviews, 9 bedrooms, 10 beds, 4.5 bathrooms
15–20 Jul