Chestertown Vacation Rentals

Compare 16 vacation rentals. Enter your trip dates to get started.
USA > New York > Chestertown

Make Chestertown your next getaway—choose from 16 great vacation rentals

Explore Our Chestertown Vacation Rentals

Explore Chestertown house rentals, cabins, chateau rentals, and more


House rentals

View 13 House rentals


View 1 Cabins

Chateau rentals

View 1 Chateau rentals

Chestertown vacation rentals for every getaway

Dog-friendly Hot tub Internet
Sagevick Cabin
1 Bedroom | 1.5 Bath | Sleeps 2

Sagevick Cabin - Chestertown, NY

$217 avg / night
Basic Adirondack Camp
3 Bedroom | 1 Bath | Sleeps 8

Basic Adirondack Camp - Chestertown, NY

$365 avg / night
Retreat on the Pond
3 Bedroom | 1 Bath | Sleeps 6

Retreat on the Pond - Chestertown, NY

$238 avg / night
Loon Lookout Chalet
4 Bedroom | 3 Bath | Sleeps 8

Loon Lookout Chalet - Chestertown, NY

$366 avg / night
The Hope House
3 Bedroom | 2 Bath | Sleeps 8 (6 Adults Max)

The Hope House - Chestertown, NY

$242 avg / night

View 11 more homes

Recent Chestertown vacation rental reviews

House is located on lakefront and you will get the best sunset views. It was very clean and equipped with all essentials. We really enjoyed our stay.
Ritesh S. | Oct 2022
Lovely log home with private access to Loon Lake for swimming, fishing and all water activities. Lake water is clear and clean. Nice campfire area right on the the shore. Beautiful view of the loons diving and calling each other. Quick access to Rt 86 north to Lake Placid area. We came as a couple celebrating our 35th wedding anniversary but the home has plenty of room for an large or extended family comfortably. Plenty of activites to do within a days driving distance in all directions.
Robert S. | Sep 2022
The house was great, the lake was beautiful, very close to everything we needed. We had a great time!
michael g. | Sep 2022
Chestertown Frequently Asked Questions

Yes, 6 of our Chestertown homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 39 of our Chestertown vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Chestertown vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Chestertown team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Chestertown, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Right off Highway 87, in the middle of the Adirondacks, you’ll find Chestertown, part of the Town of Chester hamlet. Mountain charm abounds here, and there’s plenty to do during any season. Find yourself a Chestertown vacation rental and you’ll soon be immersed in the world of colorful fall leaves, lake activities, hiking, and snowshoeing. From horseback riding to snowmobiling, there’s plenty to occupy an outdoors lover here. Hikers of all levels will enjoy the Chester Challenge, a local family-friendly hiking loop. Come experience the upstate magic of a Chestertown rental.