Chestertown Vacation Rentals

Compare 14 vacation rentals. Enter your trip dates to get started.
USA > New York > Chestertown

Make Chestertown your next getaway—choose from 14 great vacation rentals

Explore Our Chestertown Vacation Rentals

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


House rentals

View 12 House rentals

Chateau rentals

View 1 Chateau rentals


View 1 Cottages

Chestertown vacation rentals for every getaway

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

Edgewater Cabin - Chestertown, NY

$172 avg / night
Basic Adirondack Camp
3 Bedroom | 1 Bath | Sleeps 8

Basic Adirondack Camp - Chestertown, NY

$322 avg / night
Retreat on the Pond
3 Bedroom | 1 Bath | Sleeps 6

Retreat on the Pond - Chestertown, NY

$115 avg / night
Loon Lookout Chalet
4 Bedroom | 3 Bath | Sleeps 8

Loon Lookout Chalet - Chestertown, NY

$388 avg / night
The Hope House
3 Bedroom | 2 Bath | Sleeps 8 (6 Adults Max)

The Hope House - Chestertown, NY

$259 avg / night

View 9 more homes

Recent Chestertown vacation rental reviews

Loved the open floor plan and nook upstairs in the loft. Nice updated kitchen. House was secluded and quiet. Kids loved taking the hike over to the nearby lake.
Ben S. | Jan 2023
Lots of Room
Tom G. | Jan 2023
Laura T. | Dec 2022
Chestertown vacation rental FAQ

Yes, 7 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. 37 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.