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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Summer on the Lake - Berkshires near Tanglewood
3 bedrooms, 4 beds, 2 private bathrooms
13–18 Sept
,
4.96 out of 5 average rating, 74 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
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds
2–7 Aug
4.68 out of 5 average rating, 38 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
4.92 out of 5 average rating, 53 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
30 Aug – 4 Sept
4.83 out of 5 average rating, 24 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
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
23–28 Aug
4.8 out of 5 average rating, 35 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
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 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
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds
1–6 Aug
5.0 out of 5 average rating, 23 reviews
Room in Pittsfield
The Yellow Room
1 double bed
29 Aug – 3 Sept
4.84 out of 5 average rating, 89 reviews
Flat in Pittsfield
Spacious Green 2 bedroom Downtown
2 bedrooms, 4 beds
9–14 Aug
4.8 out of 5 average rating, 51 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
Guest favourite
Home in Pittsfield
Berkshire Lakehouse - 3 bedrooms - sleeps 5
3 bedrooms, 3 beds
22–27 Sept
4.92 out of 5 average rating, 49 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
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds
24–29 Aug
4.95 out of 5 average rating, 37 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