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Vacation rentals in Chestertown

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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. Gore MTN
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
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!
$226 per night
Home in Chestertown
Adirondack House on Loon Lake
Lovely Adirondack house on the shores of Loon Lake. Beautiful lake view! Great for the outdoor enthusiast or just come and relax. New dock and float great for swimming, 3 kayaks, 2 paddle boards, and 2 person canoe provided. Bring your own boat or rent from nearby Loon Lake Marina. Large deck and lakeside fire pit. Close to hiking, family friendly activities and restaurants. 3 bedroom, enclosed porch w futon, 2 bath, sleeps 8. Great for families or groups.
$365 per night

Stay near Chestertown's top sights

Photo of Main Street Ice Cream Parlor
Main Street Ice Cream Parlor50 locals recommend
Photo of The Bullhouse
The Bullhouse33 locals recommend
Photo of Tops Friendly Markets
Tops Friendly Markets28 locals recommend
Photo of Panther Mountain Inn
Panther Mountain Inn8 locals recommend
Photo of Odd Duck
Odd Duck22 locals recommend
Photo of Dynamite Hill Recreation Area
Dynamite Hill Recreation Area20 locals recommend

Other great vacation rentals in Chestertown

Home in Chestertown
Beautiful 1BR Lakefront Adirondacks | Dock
$155 per night
Private room in Chestertown
Rustic Adirondack Studio Apartment
$120 per night
Home in Chestertown
Adirondack Base Camp by Loon Lake and Gore Mt.!
$137 per night
Loft in Brant Lake
Cozy Adirondack Efficiency
$127 per night
Cabin in Chestertown
Lazy Loon Cabin- Fire pit, Hot Tub, Dock,Fireplace
$320 per night
Cottage in Chestertown
Friends Lake Adirondack Cottage
$210 per night
Chalet in Chestertown
Blue Loon Retreat -Near Gore Mountain
$174 per night
Cabin in Chestertown
Come get cozy and Ski Gore and Vermont Mtn.’s!
$180 per night
Home in Chestertown
Adirondack Lake House
$200 per night
Home in Chestertown
Adirondack 🏠 near Gore Mt, North Creek, Loon lake.
$271 per night
Loft in North Creek
Gore Mountain Studio Retreat
$115 per night
Vacation home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
$149 per night
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