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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, 155 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
30 Aug – 4 Sept
4.89 out of 5 average rating, 37 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds
11–16 Sept
4.96 out of 5 average rating, 228 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
26–31 Oct
5.0 out of 5 average rating, 35 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
25–30 Aug
4.84 out of 5 average rating, 45 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
20–25 Aug
4.65 out of 5 average rating, 46 reviews
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds
23–28 Aug
4.98 out of 5 average rating, 464 reviews
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds
23–28 Aug
4.97 out of 5 average rating, 72 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
23–28 Aug
4.92 out of 5 average rating, 324 reviews
Superhost
Room in Pittsfield
Sunny Room in Downtown Victorian
1 bed
31 Aug – 5 Sept
4.73 out of 5 average rating, 22 reviews
Home in Lenox
The Gardener's Cottage 1893 at Ventfort Hall
2 bedrooms, 2 queen beds
22–27 Aug
4.75 out of 5 average rating, 4 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
6–11 Sept
4.92 out of 5 average rating, 59 reviews
Guest favourite
Home in Pittsfield
Dancing Horse Lodge
3 bedrooms, 3 beds
23–28 Aug
4.87 out of 5 average rating, 328 reviews
Flat in Lenox
1BR Apt, private entry, kitchenette & fridge
1 bedroom, 3 beds
23–28 Aug
4.75 out of 5 average rating, 4 reviews
Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 bedrooms, 2 beds
1–6 Nov
4.84 out of 5 average rating, 194 reviews
Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
3 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 24 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds
2–7 Sept
4.97 out of 5 average rating, 71 reviews
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed
23–28 Aug
4.9 out of 5 average rating, 73 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed
25–30 Sept
4.99 out of 5 average rating, 327 reviews