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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, 153 reviews
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
26–31 Jul
4.83 out of 5 average rating, 24 reviews
Top guest favourite
Home in Pittsfield
Lake/Mountain View Getaway
2 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
4.95 out of 5 average rating, 94 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 86 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 51 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
20–25 Jul
4.67 out of 5 average rating, 36 reviews
Guest favourite
Home in Pittsfield
A Ray of Sunshine-Lakefront-New Construction- ski
5 bedrooms, 4.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 bathroom
6–11 Sept
4.99 out of 5 average rating, 316 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
4.95 out of 5 average rating, 221 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
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bathroom
20–25 Nov
4.96 out of 5 average rating, 51 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.92 out of 5 average rating, 319 reviews
Guest favourite
Cottage in Lanesborough
The Grove Lakehouse
2 bedrooms, 6 beds, 1 bathroom
8–13 Sept
4.86 out of 5 average rating, 7 reviews
Home in Lenox
7 Minute Walk to Tanglewood from New 2BR Home
2 bedrooms, 2 queen beds, 1.5 bathrooms
25–30 Jul
New place to stay
Guest favourite
Guest suite in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
1 bedroom, 2 beds, 1 bathroom
22–27 Jul
4.81 out of 5 average rating, 95 reviews
Flat in Lenox
1BR Apt, private entry, kitchenette & fridge
1 bedroom, 4 beds, 1 bathroom
20–25 Jul
New place to stay
Guest favourite
Room in Pittsfield
Sunny Room in Downtown Victorian
1 bed, 2 bathrooms
21–26 Jul
4.79 out of 5 average rating, 19 reviews