Chestertown Vacation Rentals

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USA > New York > Chestertown

Make Chestertown your next getaway—choose from 19 great vacation rentals

Explore Our Chestertown Vacation Rentals

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


House rentals

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Chateau rentals

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Chestertown vacation rentals for every getaway

Dog-friendly Hot tub Internet
The Hope House 3D Tour
3 Bedroom | 2 Bath | Sleeps 8 (6 Adults Max)

The Hope House - Chestertown, NY

From $123
Hideaway Chalet 3D Tour
3 Bedroom | 2 Bath | Sleeps 6

Hideaway Chalet - Chestertown, NY

From $239
Pine's Way Camp 3D Tour
4 Bedroom | 2 Bath | Sleeps 6

Pine's Way Camp - Chestertown, NY

From $123
Retreat on the Pond 3D Tour
3 Bedroom | 1 Bath | Sleeps 6

Retreat on the Pond - Chestertown, NY

From $122
Whit's End 3D Tour
4 Bedroom | 3.5 Bath | Sleeps 8

Whit's End - Chestertown, NY

From $188

View 14 more homes

Recent Chestertown vacation rental reviews

The Hope House was everything we depicted when we searched for a ski house rental. From the secluded area down to the wood burning stove, it felt like everything we imagined. Thank you for the experience, we will be back.
Richard M. | Jan 2022
We had a wonderful vacation in this house. The area is very quiet and beautiful. The house is clean and warm. The location is closed to the dynamite hill where you can have fun on tubing or other winter activities. We will definitely rent this house again.
Ruslan M. | Jan 2022
Pictures on the internet do not do this property justice. Well equipped and comfortable, spotlessly clean. Quiet and private but close to shops. We were delighted to find such a modern and clean space right near where we wanted to be. It was the perfect place for our ski trip and such a great value. Very comfortable would definitely recommend. The best Airbnb we’ve ever been to!
Marian S. | Jan 2022

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.