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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. 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
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
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

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

Rental unit in Chestertown
Rustic Adirondack Studio Apartment
$120 per night
Cabin in Chestertown
Chestertown Hideaway w/ Lake & Beach Access!
$199 per night
Home in Chestertown
3BR Lakefront Adirondacks | Dock | Firepit
$229 per night
Home in Chestertown
North Pine Lodge @ Loon Lake, ADK adventure awaits
$449 per night
Townhouse in Chestertown
Bright summer retreat-beach, hike, pickleball,golf
$201 per night
Home in Chestertown
Adirondack 🏠 near Gore Mt, North Creek, Loon lake.
$271 per night
Home in Chestertown
Child-friendly 3BR Adirondacks | Fireplace
$305 per night
Home in Chestertown
Beautiful 1BR Lakefront Adirondacks | Dock
$156 per night
Private room in North Creek
North Creek & Gore Mtn Private Adirondack Ensuite
$99 per night
Home in Chestertown
Rustic Adirondacks Home w/ Hot Tub & Lake Access!
$176 per night
Home in Chestertown
Private Lake Front House-20 min Lake George & Gore
$326 per night
Vacation home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
$149 per night

Other types of stays on Airbnb

  1. Airbnb
  2. United States
  3. New York
  4. Warren County
  5. Chestertown