A historic building with a prominent tower and an American flag.

Pittsfield houses

We found 34 houses — enter your dates for availability

Explore Pittsfield house rentals

Image of PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

Premier Host

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

Sleeps 24 · 7 bedrooms · 5 bathrooms

Image of Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area

Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area

Sleeps 7 · 2 bedrooms · 1 bathroom

Image of Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

Sleeps 8 · 3 bedrooms · 2 bathrooms

Image of Stay Steps from Pine Lake | Family Cabin & Scenic Grounds | Pool & Kid's Area

Stay Steps from Pine Lake | Family Cabin & Scenic Grounds | Pool & Kid's Area

Sleeps 6 · 2 bedrooms · 1 bathroom

Image of Pine Lakes Adventure Base | Swim, Fish & Explore the Great Outdoors

Pine Lakes Adventure Base | Swim, Fish & Explore the Great Outdoors

Sleeps 8 · 2 bedrooms · 1 bathroom

Image of Family-friendly and perfect for large groups and family reunions

Family-friendly and perfect for large groups and family reunions

Sleeps 40 · 8 bedrooms · 6 bathrooms

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