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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds, 1 private bathroom
7–12 Sept
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4.93 out of 5 average rating, 109 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
5.0 out of 5 average rating, 30 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
4.68 out of 5 average rating, 38 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
4.83 out of 5 average rating, 24 reviews, 2 beds, 3 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
4.95 out of 5 average rating, 222 reviews, 3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
4.92 out of 5 average rating, 52 reviews, 1 bed, 2 bathrooms
23–28 Aug
Guest favourite
Flat in Pittsfield
Marie's Place
4.92 out of 5 average rating, 321 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
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
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
5.0 out of 5 average rating, 87 reviews, 1 queen bed, 1 bathroom
24–29 Aug
Room in Pittsfield
The Yellow Room
4.84 out of 5 average rating, 89 reviews, 1 double bed, 1.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
5.0 out of 5 average rating, 43 reviews, 4 bedrooms, 4 beds, 1.5 bathrooms
31 Aug – 5 Sept
Top guest favourite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5.0 out of 5 average rating, 23 reviews, 5 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
4.97 out of 5 average rating, 121 reviews, 3 bedrooms, 3 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
4.97 out of 5 average rating, 68 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
23–28 Aug
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
Home in New Lebanon
Spacious 4BR Summer Escape | Queechy Lake Passes
4.76 out of 5 average rating, 17 reviews, 4 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Home in Lanesborough
New built - Split level house in the Berkshires
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
Top guest favourite
Home in Lanesborough
The Pond House
4.96 out of 5 average rating, 52 reviews, 3 bedrooms, 4 beds, 1 bathroom
20–25 Nov
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
4.99 out of 5 average rating, 321 reviews, 1 bedroom, 1 bed, 1 bathroom
6–11 Sept