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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Berkshire Lakehouse - 3 bedrooms - sleeps 5
3 bedrooms, 3 beds, 1 private bathroom
22–27 Sept
,
4.92 out of 5 average rating, 50 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
30 Aug – 4 Sept
4.89 out of 5 average rating, 37 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
25–30 Aug
4.84 out of 5 average rating, 45 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
6–11 Sept
4.92 out of 5 average rating, 59 reviews
Superhost
Room in Pittsfield
Sunny Room in Downtown Victorian
1 bed, 2 bathrooms
31 Aug – 5 Sept
4.73 out of 5 average rating, 22 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, 464 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
4.96 out of 5 average rating, 228 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
20–25 Aug
4.65 out of 5 average rating, 46 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
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 queen bed, 1 bathroom
12–17 Sept
4.92 out of 5 average rating, 138 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
3–8 Oct
5.0 out of 5 average rating, 91 reviews
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed, 1 bathroom
23–28 Aug
4.9 out of 5 average rating, 73 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 35 reviews
Guest favourite
Room in Becket
East b.r. in upstairs suite of open plan home
1 bathroom
23–28 Aug
4.87 out of 5 average rating, 261 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 621 reviews
Top guest favourite
Flat in New Lebanon
Folk Art Studio: 1-bedroom near the Berkshires
1 bedroom, 2 beds, 1 bathroom
4–9 Sept
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 bathroom
25–30 Sept
4.99 out of 5 average rating, 327 reviews
Room in Pittsfield
The Yellow Room
1 double bed, 1.5 bathrooms
29 Aug – 3 Sept
4.83 out of 5 average rating, 92 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 324 reviews