Search results; Over 1,000 homes in Pittsfield

Serviced apartment in Pittsfield
One Bedroom Apartment with a full kitchen
1 bedroom, 2 beds, 1 bathroom
6–11 Jul
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4.83 out of 5 average rating, 6 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
5.0 out of 5 average rating, 14 reviews, 2 beds, 3 bathrooms
12–17 Jul
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
4.77 out of 5 average rating, 30 reviews, 1 bed, 2 bathrooms
5–10 Jul
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
4.64 out of 5 average rating, 28 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Jul
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
4.98 out of 5 average rating, 456 reviews, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
5.0 out of 5 average rating, 25 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
4.95 out of 5 average rating, 215 reviews, 3 bedrooms, 5 beds, 2 bathrooms
6–11 Jul
Top guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
4.94 out of 5 average rating, 47 reviews, 1 bed, 2 bathrooms
23–28 Aug
Home in New Lebanon
Above the Clouds Mountain Retreat
New place to stay, 3 bedrooms, 3 beds, 4 bathrooms
14–19 Jul
Guest favourite
Flat in Pittsfield
Marie's Place
4.91 out of 5 average rating, 315 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 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
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
4.99 out of 5 average rating, 310 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Guest favourite
Guest suite in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
4.8 out of 5 average rating, 92 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Jul
Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Berkshires
4.89 out of 5 average rating, 122 reviews, 1 bed, 1 bathroom
5–10 Jul
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
4.97 out of 5 average rating, 66 reviews, 2 bedrooms, 2 beds, 1 bathroom
5–10 Nov
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
5.0 out of 5 average rating, 82 reviews, 1 queen bed, 1 bathroom
24–29 Aug
Top guest favourite
Home in Lanesborough
Historic Stone Church in The Berkshires
4.98 out of 5 average rating, 81 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
5–10 Jul