Chestertown Vacation Rentals

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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

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Chateau rentals

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Chestertown vacation rentals for every getaway

Dog-friendly Internet Lake view
The Hope House
3 Bed | 2 Bath | Sleeps 8 (6 Adults Max)

The Hope House - Chestertown, NY

From $169
Hideaway Chalet 3D Tour
3 Bed | 2 Bath | Sleeps 6

Hideaway Chalet - Chestertown, NY

From $279
Whit's End 3D Tour
4 Bed | 3.5 Bath | Sleeps 8

Whit's End - Chestertown, NY

From $273
Pine's Way Camp 3D Tour
4 Bed | 2 Bath | Sleeps 6

Pine's Way Camp - Chestertown, NY

From $139
Affordable Lake Rights 3D Tour
4 Bed | 1.5 Bath | Sleeps 8

Affordable Lake Rights - Chestertown, NY

From $124

View 11 more homes

Recent Chestertown vacation rental reviews

The house was perfect! Clean - well stocked. Location private and beautiful view. I would come back in a heartbeat!
Judith U. | Sep 2021
A great Chalet, nice and clean , updated, perfectly located 25 min from everything.. enjoyed this place alot.. cant wait to come back
william r. | Sep 2021
Hideaway Chalet exceeded our 5* expectations and contributed to our amazing experience in the Adirondacks. Let’s start with the beginning: we’ve traveled from Virginia Beach and after a long trip the check-in was super easy. The house was very welcoming and each member of my family was mesmerized by how super clean each corner was. The kitchen is very well equipped and has everything you need for cooking. We admired the hand picked decorations around the house as well. We loved to spend the nights outside near the fire pit or in the game room. This is perfect location for a lot of activities around the place: hiking and/or biking on Gore Mountain, fishing, paddling and/or swimming on the lake near the cabin—we chose to spend the time on the small beach. Of course, being very close to Lake George we chose to go as well.
Adrian P. | Sep 2021

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.