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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
2 beds, 3 bathrooms
12–17 Jul
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
12–17 Jul
4.94 out of 5 average rating, 47 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
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, 82 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
Room in Pittsfield
The Yellow Room
1 double bed, 1.5 bathrooms
27 Jul – 1 Aug
4.84 out of 5 average rating, 85 reviews
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 104 reviews
Guest favourite
Home in Pittsfield
Elmer Estate
3 bedrooms, 3 beds, 1 bathroom
21–26 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 310 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bathroom
9–14 Dec
4.96 out of 5 average rating, 49 reviews
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
4.94 out of 5 average rating, 35 reviews
Guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 120 reviews
Guest favourite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
3 bedrooms, 4 beds, 1 bathroom
16–21 Sept
4.93 out of 5 average rating, 133 reviews
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, 214 reviews
Guest favourite
Flat in Pittsfield
Beautiful & Serene Getaway
3 bedrooms, 2 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 197 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
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 15 reviews