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.

Guest favorite
Home in Wevertown
A Cozy Creekside Getaway minutes from Gore Mtn.
This quiet getaway is perfect for the family or a small group of friends. This two bedroom, two full bath home is situated on a quiet dirt road right in the heart of the Adirondacks and is perfect for the outdoor enthusiast. It offers easy access to the High Peaks and is just 5 miles from both Gore Mtn. and The Revolution Rail. Opportunities such as hiking, mountain biking, kayaking, rafting and fishing are all within 15 minutes of our location. SEASONAL DISCOUNTS AVAILABLE! Please inquire.
Apr 26 – May 3
$108 per night
4.98 out of 5 average rating, 121 reviews
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
Nov 21 – 28
$125 per night
5.0 out of 5 average rating, 151 reviews
Guest favorite
Home in Adirondack
Adirondack Owl's Nest Guest House
Our Adirondack Guest House is centrally located to many nearby attractions the region has to offer. Located on 10 wooded acres, just minutes off Northway I-87. Only 2 miles from Schroon Lake boat launch and Word of Life. Minutes to Brant Lake & Loon Lake. A short drive to beautiful Lake George and nearby Gore Mountain. The area offers: swimming, hiking, bicycling, fishing, golfing, canoeing & kayaking, river tubing, adventure course, rodeos, skiing, snowshoeing, sledding, & snowmobiling.
Jan 28 – Feb 4
$215 per night
5.0 out of 5 average rating, 141 reviews

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
Apartment in Chestertown
Rustic Adirondack Studio Apartment
Apr 16 – 23
$123 per night
5.0 out of 5 average rating, 86 reviews
Guest favorite
Home in Chestertown
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Sep 1 – 8
$328 per night
4.95 out of 5 average rating, 64 reviews
Guest favorite
Barn in Chestertown
Adirondack Base Camp by Loon Lake and Gore Mt.!
Dec 3 – 10
$158 per night
4.98 out of 5 average rating, 43 reviews
Guest favorite
Vacation home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
Jun 12 – 19
$140 per night
5.0 out of 5 average rating, 23 reviews
Guest favorite
Chalet in Chestertown
Blue Loon - Season Rental Available- near Gore
Apr 26 – May 3
$150 per night
4.89 out of 5 average rating, 44 reviews
Guest favorite
Cabin in Warrensburg
Bearpine Cottage
Sep 25 – Oct 2
$120 per night
4.93 out of 5 average rating, 28 reviews
Guest favorite
Guesthouse in Brant Lake
Arrowhead @ Brant Lake
Jul 10 – 17
$138 per night
4.98 out of 5 average rating, 85 reviews
Guest favorite
Barn in Chestertown
Posh Camp the Quintessential Adirondack Cabin
Jan 19 – 26
$240 per night
4.99 out of 5 average rating, 72 reviews
Guest favorite
Home in Chestertown
Blue Bay Retreat - Loon Lake Lakefront w/ Hot Tub
Dec 5 – 12
$595 per night
5.0 out of 5 average rating, 15 reviews
Guest favorite
Home in Chestertown
North Pine Lodge @ Loon Lake, ADK adventure awaits
Oct 22 – 29
$442 per night
4.92 out of 5 average rating, 65 reviews
Guest favorite
Cabin in Johnsburg
2 bdrm ADK cabin 10 mins to GORE MTN
Dec 29 – Jan 5
$120 per night
4.97 out of 5 average rating, 64 reviews
Guest favorite
Home in Chestertown
Chestertown Charm close to Gore Mt. Come ski!
Aug 19 – 26
$204 per night
4.85 out of 5 average rating, 20 reviews

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