Pittsfield country houses
We found 9 country houses — enter your dates for availability
Explore Pittsfield mansion rentals
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Sleeps 24 · 7 bedrooms · 5 bathrooms
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
Sleeps 8 · 3 bedrooms · 2 bathrooms
Stay Steps from Pine Lake | Family Cabin & Scenic Grounds | Pool & Kid's Area
Sleeps 6 · 2 bedrooms · 1 bathroom
Guesthouse Sleeps 7 Kitchen Washer Dryer Dishwasher New Queens
Sleeps 6 · 1 bathroom
Lovers’ Lakeside Love Nest Cozy Retreat on Pittsfields Serene Lake.
Sleeps 8 · 3 bedrooms · 2 bathrooms
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
Sleeps 7 · 2 bedrooms · 1 bathroom
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value