Vacation rentals in Chestertown

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chestertown

Guests agree: these stays are highly rated for location, cleanliness, and more.

Barn in Chestertown

ADK RED BARN off I-87. Cozy clean modern. Patio.

Relax in this cozy and modern barn! With a little rustic flair the inside is loaded with luxurious amenities. 1min off I-87 1min Schroon River 2mins Loon Lake 5mins Brant Lake 25mins Gore Mountain 25mins Lake George 1hr+ Lake Placid Tons of nearby hikes! This is the perfect place to rest your head after your ADK day. Play games, read, cook, or chill. There's a full kitchen, dining area, loft with 2 sofa beds, a private bedroom, desk, spa-like shower & an outdoor lawn, patio & seasonal fire pit.

$160 per night

SUPERHOST

Home in Chestertown

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

Welcome to Jackson's Lodge! Looking for an Adirondack escape for your family and friends in any season? Nestled in a private, 4 acre park like setting in the Southeast ADKs, this cozy mid century modern cabin will show you what upstate NY living is all about. After exploring the best the ADKs have to offer, come soak in the hot tub, unwind in the cedar screened-in porch, or pull up a chair to the natural stone fire pit. Roast some 'smores, take in the night sky, and let your stress melt away!

$228 per night

SUPERHOST

Rental unit in Chestertown

Lily Pad South at Loon Lake near Gore Mountain

Lily Pad South is nestled in the Adirondack Mountains of upstate NY. This two bedroom unit is super clean and a great place to relax. The property is rural, yet centrally located to 5 lakes, skiing at Gore Mountain, and famous Lake George Village, with easy highway access only five minutes away. Sleeps 4 adults plus 1 infant. If you have a smaller or larger group, please inquire about the availability of a 4 bedroom house or the adjacent 7 bedroom house.

$87 per night

SUPERHOST