filters

Search results; Over 1,000 homes in Pittsfield

Descriptions are based on details hosts provide
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 private bathrooms
26–31 Jul
,
4.95 out of 5 average rating, 218 reviews
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
26–31 Jul
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Pittsfield
New lakefront home with rooftop lake views
5 bedrooms, 4.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Home in Pittsfield
1847 farmhouse with a wraparound porch
4 bedrooms, 4 beds, 1.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Home in Pittsfield
Newly renovated with cathedral ceilings, near Tanglewood
5 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
4.95 out of 5 average rating, 75 reviews
Top guest favourite
Room in Pittsfield
Sunrooms, garden, and fire pit in Berkshires
1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 86 reviews
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 105 reviews
Top guest favourite
Home in Pittsfield
Lakefront with a pool and kayaks
6 bedrooms, 10 beds, 4.5 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 81 reviews
Guest favourite
Home in Pittsfield
Berkshire Views
6 bedrooms, 7 beds, 4 bathrooms
13–18 Sept
5.0 out of 5 average rating, 19 reviews
Guest favourite
Room in Pittsfield
Drag-themed Queen Anne Victorian mansion
1 bed, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 48 reviews
Guest favourite
Home in Pittsfield
Restored retreat on 12 private acres
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
4.94 out of 5 average rating, 36 reviews
Guest favourite
Home in Pittsfield
Mountain views, hot tub, and a fireplace
5 bedrooms, 8 beds, 3 bathrooms
27 Jul – 1 Aug
4.97 out of 5 average rating, 152 reviews
Top guest favourite
Home in Pittsfield
Pond-front with a fireplace and kayak
2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Pittsfield
Colonial home with a porch and yard
3 bedrooms, 3 beds, 1.5 bathrooms
23–28 Aug
4.97 out of 5 average rating, 65 reviews
Top guest favourite
Room in Pittsfield
Spacious suite with homemade breakfast included
2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 460 reviews
Guest favourite
Flat in Pittsfield
Berkshire’s Sweet Spot- Pool and Spa- Discount Now
3 bedrooms, 4 beds, 1.5 bathrooms
2–7 Aug
4.93 out of 5 average rating, 84 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 317 reviews
Top guest favourite
Home in Pittsfield
Lake views from 3 decks with fire pit
4 bedrooms, 6 beds, 4 bathrooms
13–18 Sept
4.94 out of 5 average rating, 47 reviews
Room in Pittsfield
1800s artist’s home near downtown
1 double bed, 1.5 bathrooms
26–31 Aug
4.84 out of 5 average rating, 87 reviews