Chestertown Vacation Rentals

Compare 13 vacation rentals.
USA > New York > Chestertown

Make Chestertown your next getaway

Explore Our Chestertown Vacation Rentals

Explore Chestertown house rentals, cottages, farmhouses, and more


House rentals

View 10 House rentals


View 2 Cottages


View 1 Farmhouses

Popular amenities for Chestertown vacation rentals

Dog-friendly Hot tub Internet
Whit's End
4 Bedroom | 3.5 Bath | Sleeps 8

Whit's End - Chestertown, NY

$300 avg / night
Loon Lodge
5 Bedroom | 3 Bath | Sleeps 10

Loon Lodge - Chestertown, NY

$321 avg / night
Basic Adirondack Camp
3 Bedroom | 1 Bath | Sleeps 6

Basic Adirondack Camp - Chestertown, NY

$222 avg / night
River Road Retreat
3 Bedroom | 1 Bath | Sleeps 5

River Road Retreat - Chestertown, NY

$150 avg / night
Pine's Way Camp
4 Bedroom | 2 Bath | Sleeps 6

Pine's Way Camp - Chestertown, NY

$181 avg / night

View 8 more homes

Recent Chestertown guest reviews

Quaint, rustic, comfortable- the ambiance of the house and property fostered a peaceful, relaxing, and pleasant atmosphere while at the same time provided the outlets for kayaking, fishing, hiking. A step back in time but with all the modern conveniences.
Gary S. | Jun 2024
Beautiful house. Everything was perfect.
Janine F. | Jun 2024
Location, layout and size
Antonio G. | Jun 2024
Chestertown vacation rental FAQ

Yes, 15 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. 56 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.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons 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.