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Search results; Over 1,000 homes in Pittsfield

Descriptions are based on details hosts provide
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 beds, 1 shared bathroom
9–14 Aug
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4.91 out of 5 average rating, 317 reviews
Top guest favourite
Room in Pittsfield
Themed room in a Queen Anne Victorian
5.0 out of 5 average rating, 17 reviews, 2 beds, 3 bathrooms
26–31 Jul
Guest favourite
Home in Pittsfield
A Ray of Sunshine-Lakefront-New Construction- ski
5.0 out of 5 average rating, 35 reviews, 5 bedrooms, 4.5 bathrooms
26–31 Jul
Top guest favourite
Home in Pittsfield
1847 farmhouse with a wraparound porch
5.0 out of 5 average rating, 41 reviews, 4 bedrooms, 4 beds, 1.5 bathrooms
24–29 Aug
Top guest favourite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
4.95 out of 5 average rating, 75 reviews, 5 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Room in Pittsfield
Sunrooms, garden, and fire pit in Berkshires
5.0 out of 5 average rating, 86 reviews, 1 queen bed, 1 bathroom
24–29 Aug
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
4.95 out of 5 average rating, 218 reviews, 3 bedrooms, 5 beds, 2 bathrooms
26–31 Jul
Guest favourite
Room in Pittsfield
Drag-themed Queen Anne Victorian mansion
4.92 out of 5 average rating, 48 reviews, 1 bed, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Pittsfield
Lakefront with a pool and kayaks
4.98 out of 5 average rating, 81 reviews, 6 bedrooms, 10 beds, 4.5 bathrooms
26 Sept – 1 Oct
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
4.93 out of 5 average rating, 105 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
4.98 out of 5 average rating, 460 reviews, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Home in Pittsfield
Colonial home with a porch and yard
4.97 out of 5 average rating, 65 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
23–28 Aug
Guest favourite
Home in Pittsfield
Restored retreat on 12 private acres
4.94 out of 5 average rating, 36 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
Top guest favourite
Home in Pittsfield
Pond-front with a fireplace and kayak
5.0 out of 5 average rating, 26 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
Guest favourite
Home in Pittsfield
Mountain views, hot tub, and a fireplace
4.97 out of 5 average rating, 152 reviews, 5 bedrooms, 8 beds, 3 bathrooms
27 Jul – 1 Aug
Guest favourite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
4.93 out of 5 average rating, 133 reviews, 3 bedrooms, 4 beds, 1 bathroom
28 Oct – 2 Nov
Guest favourite
Flat in Pittsfield
Berkshire’s Sweet Spot- Pool and Spa- Discount Now
4.93 out of 5 average rating, 84 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
2–7 Aug
Guest favourite
Home in Pittsfield
Meadow and mountain views on 2 acres
5.0 out of 5 average rating, 19 reviews, 6 bedrooms, 7 beds, 4 bathrooms
13–18 Sept
Flat in Pittsfield
Petite Paris
4.82 out of 5 average rating, 38 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
1–6 Aug