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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.

Guest favorite
Cabin in Warrensburg
Romantic Lake George Getaway~Chickadee Hill
*Romantic getaway nestled in the Adirondack Mountains, just 15 minutes to Lake George *Vintage Record Player, Farm Fresh Eggs and pollinator gardens *A dreamy escape into nature where you will wake up and feel like you are still dreaming *This is not just any five star stay step outside we have millions our night sky is breathtaking *We strive for our guests to have nothing less than a five star experience, as you can see by our reviews Chickadee is decorated for Christmas Nov 1st-January
Sep 27 – Oct 4
$124 per night
Guest favorite
Home in Chestertown
The Stone Lodge on Blythewood Island in Loon Lake
Looking for an all-season getaway in the Adirondacks? Come enjoy our lake and mountain views at the historic Stone Lodge on Blythewood Island in Loon Lake in Chestertown, NY. Our family has lived on the Island for more than 60 years. We welcome you to join us! The Stone Lodge was brought back to its original ambiance 7 years ago, when the Monroe family made it a place where others could enjoy the beauty, sights and sounds of nature from a beautiful authentic Adirondack retreat.
Sep 19 – 26
$350 per night
Guest favorite
Barn in Chestertown
Red Barn Guesthouse. Cozy modern stay. Hot Tub!
Relax in this cozy 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 Tons of nearby hikes! This is the perfect place to rest your head. Soak in the Hot Tub. There's a full kitchen, dining area, loft with 2 sofa beds, a private bedroom, desk, spa-like shower & an outdoor lawn, & seasonal fire pit. PLEASE READ HOUSE RULES BEFORE BOOKING
Jul 30 – Aug 6
$329 per night

Popular amenities for Chestertown vacation rentals

Stay near Chestertown's top sights

Main Street Ice Cream Parlor50 locals recommend
The Bullhouse33 locals recommend
Tops Friendly Markets28 locals recommend
Panther Mountain Inn8 locals recommend
Odd Duck21 locals recommend
Dynamite Hill Recreation Area20 locals recommend

Other great vacation rentals in Chestertown

Guest favorite
Home in Adirondack
Adirondack Owl's Nest Guest House
Dec 30 – Jan 6
$215 per night
Guest favorite
Apartment in Chestertown
Rustic Adirondack Studio Apartment
Nov 13 – 20
$123 per night
Guest favorite
Barn in Chestertown
Adirondack Base Camp by Loon Lake and Gore Mt.!
Oct 31 – Nov 7
$168 per night
Guest favorite
Apartment in Chestertown
Lily Pad North at Loon Lake near Gore Mountain
Sep 30 – Oct 7
$112 per night
Guest favorite
Home in Chestertown
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Feb 6 – 13
$298 per night
Guest favorite
Cabin in Johnsburg
2 bdrm ADK cabin 10 mins to GORE MTN
Jan 19 – 26
$113 per night
Guest favorite
Guesthouse in Brant Lake
Arrowhead @ Brant Lake
Jul 21 – 28
$138 per night
Guest favorite
Home in Chestertown
Blue Bay Retreat - Loon Lake Lakefront w/ Hot Tub
Dec 29 – Jan 5
$595 per night
Guest favorite
Cabin in Warrensburg
Bearpine Cottage
Dec 16 – 23
$131 per night
Guest favorite
Vacation home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
Aug 10 – 17
$140 per night
Guest favorite
Home in Chestertown
North Pine Lodge @ Loon Lake, ADK adventure awaits
Nov 26 – Dec 3
$441 per night
Guest favorite
Barn in Chestertown
Posh Camp the Quintessential Adirondack Cabin
Oct 10 – 17
$240 per night

Quick stats about vacation rentals in Chestertown

Total rentals

10 properties

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

10 properties include access to wifi

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

250 reviews

Nightly prices starting at

$90 before taxes and fees

Destinations to explore

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