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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 bed, 1 private bathroom
7–12 Sept
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4.92 out of 5 average rating, 133 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, 30 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
4.96 out of 5 average rating, 223 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 bathroom
6–11 Sept
4.99 out of 5 average rating, 322 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
23–28 Aug
4.91 out of 5 average rating, 55 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.92 out of 5 average rating, 321 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
30 Aug – 4 Sept
4.85 out of 5 average rating, 26 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
23–28 Aug
4.81 out of 5 average rating, 37 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.99 out of 5 average rating, 311 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
Guest favourite
Cottage in Lanesborough
Wildlife Lakeside Cottage; views/wildlife
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Aug
4.85 out of 5 average rating, 297 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
10–15 Aug
4.97 out of 5 average rating, 69 reviews
Home in New Lebanon
Spacious 4BR Summer Escape | Queechy Lake Passes
4 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
4.78 out of 5 average rating, 18 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 87 reviews
Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 121 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
5–10 Aug
4.7 out of 5 average rating, 40 reviews
Top guest favourite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 23 reviews
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bathroom
20–25 Nov
4.96 out of 5 average rating, 52 reviews