Pittsfield Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Pittsfield

Don't see what you're looking for?
See all available properties in Pittsfield
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Pittsfield Vacation Rentals essential information

Accommodation
111 Vacation Rentals
Lowest Price
$205
Highest Price
$703
Popular accommodation
Peek N' Peak Resort, Ski-in/Ski-out, on golf course, Clymer, NY Ski Birdie Lodge, Creek Side Cottage with Lake Views, Lake Access, Dock and Secluded Yard, Chautauqua Lake Front Property - Short Walk to the Village of Bemus Point!, Secluded Chautauqua Lake House, private dock & beach, short stroll to town!, Beautiful Pet friendly cottage by the Stow Ferry, Quaint historic home in the heart of Bemus Point Village- a stroll to the water!, Comedy House 4 bedroom Chautauqua Lake Jamestown lakewood NY, 3 Bedroom Cottage on the Shores of Chautauqua Lake, Four Seasons Lodge - Ski In/Out - Xmas/Thanksgiving Avail. - 5 Bdrm., Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms , Room for the whole family at this Chautauqua Institution home!, Home away from Home in Jamestown NY