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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 private bathroom
23–28 Aug
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4.99 out of 5 average rating, 310 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
12–17 Jul
5.0 out of 5 average rating, 14 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
5–10 Jul
4.77 out of 5 average rating, 30 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
4.64 out of 5 average rating, 28 reviews
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 456 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, 25 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Jul
4.91 out of 5 average rating, 315 reviews
Top guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
23–28 Aug
4.94 out of 5 average rating, 47 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, 83 reviews
Home in New Lebanon
Above the Clouds Mountain Retreat
3 bedrooms, 3 beds, 4 bathrooms
14–19 Jul
New place to stay
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
6–11 Jul
4.95 out of 5 average rating, 215 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
5–10 Nov
4.97 out of 5 average rating, 67 reviews
Room in Pittsfield
The Yellow Room
1 double bed, 1.5 bathrooms
27 Jul – 1 Aug
4.84 out of 5 average rating, 86 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds, 2 bathrooms
18–23 Aug
4.99 out of 5 average rating, 308 reviews
Guest favourite
Guest suite in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
4.8 out of 5 average rating, 92 reviews
Top guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 121 reviews
Guest favourite
Farm stay in New Lebanon
NEW RENO - Chalet-style farm loft near Tanglewood
1 bedroom, 3 beds, 1 bathroom
5–10 Jul
4.91 out of 5 average rating, 66 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