Vacation rentals in Chestertown

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Top-rated vacation rentals in Chestertown

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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

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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

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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