filters

Search results; Over 1,000 homes in Pittsfield

Descriptions are based on details hosts provide
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 private bathroom
6–11 Sept
,
4.99 out of 5 average rating, 315 reviews
Top guest favourite
Room in Pittsfield
Themed room in a Queen Anne Victorian
2 beds, 3 bathrooms
26–31 Jul
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Pittsfield
A Ray of Sunshine-Lakefront-New Construction- ski
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
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
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
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 48 reviews
Guest favourite
Home in Pittsfield
Grand piano and game room near Tanglewood
3 bedrooms, 5 beds, 2 bathrooms
26–31 Jul
4.95 out of 5 average rating, 218 reviews
Top guest favourite
Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
6 bedrooms, 10 beds, 4.5 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 81 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
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 460 reviews
Guest favourite
Flat in Pittsfield
Newly renovated, minutes from ski and downtown
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
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
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
23–28 Aug
4.97 out of 5 average rating, 65 reviews
Guest favourite
Home in Pittsfield
Solar home with heated floors and porch
3 bedrooms, 4 beds, 1 bathroom
28 Oct – 2 Nov
4.93 out of 5 average rating, 133 reviews
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
4.94 out of 5 average rating, 36 reviews
Guest favourite
Home in Pittsfield
Hidden Oasis in the Mountains by Evergreen Home
5 bedrooms, 8 beds, 3 bathrooms
27 Jul – 1 Aug
4.97 out of 5 average rating, 152 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
Top guest favourite
Home in Pittsfield
Grand Berkshire Manor By Evergreen Home
5 bedrooms, 8 beds, 4.5 bathrooms
26–31 Jul
4.99 out of 5 average rating, 76 reviews