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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Dancing Horse Lodge
3 bedrooms, 3 beds, 1 private bathroom
23–28 Aug
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4.87 out of 5 average rating, 325 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
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
9–14 Aug
4.96 out of 5 average rating, 223 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
23–28 Aug
4.91 out of 5 average rating, 54 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
5–10 Aug
4.69 out of 5 average rating, 39 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
9–14 Aug
4.92 out of 5 average rating, 321 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed
6–11 Sept
4.99 out of 5 average rating, 321 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
30 Aug – 4 Sept
4.84 out of 5 average rating, 25 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
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
20–25 Sept
4.99 out of 5 average rating, 311 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed
24–29 Aug
5.0 out of 5 average rating, 87 reviews
Top guest favourite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds
1–6 Aug
5.0 out of 5 average rating, 23 reviews
Guest favourite
Cottage in Lanesborough
Wildlife Lakeside Cottage; views/wildlife
3 bedrooms, 4 beds
23–28 Aug
4.85 out of 5 average rating, 297 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds
9–14 Aug
4.97 out of 5 average rating, 121 reviews
Room in Pittsfield
The Yellow Room
1 double bed
29 Aug – 3 Sept
4.84 out of 5 average rating, 89 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, 68 reviews
Home in Lanesborough
New built - Split level house in the Berkshires
3 bedrooms, 5 beds
1–6 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds
2–7 Aug
5.0 out of 5 average rating, 12 reviews