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

housing_type_house.jpg

House rentals

View 14 House rentals
housing_type_cabin.jpg

Cabins

View 1 Cabins

Chateau rentals

View 1 Chateau rentals

Chestertown vacation rentals for every getaway

Popular
Dog-friendly Internet Lake view
Hideaway Chalet 3D Tour
3 Bed | 2 Bath | Sleeps 6

Hideaway Chalet - Chestertown, NY

From $279
Loon Lookout Chalet 3D Tour
4 Bed | 3.5 Bath | Sleeps 8

Loon Lookout Chalet - Chestertown, NY

From $207
Lakeside Vibes 3D Tour
3 Bed | 1 Bath | Sleeps 6

Lakeside Vibes - Chestertown, NY

From $203
Basic Adirondack Camp 3D Tour
3 Bed | 1 Bath | Sleeps 8

Basic Adirondack Camp - Chestertown, NY

From $187
Pine's Way Camp 3D Tour
4 Bed | 2 Bath | Sleeps 6

Pine's Way Camp - Chestertown, NY

From $147

View 11 more homes

Recent Chestertown vacation rental reviews

My husband and I took our first vacation post-covid and Sagevick Cabin was the perfect spot for it! Such a perfect view - just what I hoped it would be. It truly looks just like the pictures. I went swimming right off the beach in the back yard, we went kayaking, we saw and heard plenty of loons. The lake was quiet - even when there was boating ‘traffic’. We made a bonfire. The cabin was amazing - comfy beds, comfy couches, clean. Not the musty creaky cabin that I was afraid of - quite the opposite! I’m almost afraid to submit this glowing review for fear that it will not be available next time I want to rent it - and believe me, there will be a next time.
Christine P. | None
Photos show exactly the feel of the cabin: clean and cozy. Kitchen stock with all your needs. The sandy beach on Loon lake was nice!
Linda C. | None
We found the home peaceful and stocked with everything we needed.
Karen C. | None

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.