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

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House rentals

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Cottages

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Farmhouses

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Chestertown vacation rentals for every getaway

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

Whit's End - Chestertown, NY

$464 avg / night
4.87 (30)
Loon Lodge
5 Bed | 3 Bath | Sleeps 10

Loon Lodge - Chestertown, NY

$645 avg / night
4.57 (49)
Basic Adirondack Camp
3 Bed | 1 Bath | Sleeps 6

Basic Adirondack Camp - Chestertown, NY

$371 avg / night
4.15 (20)
River Road Retreat
3 Bed | 1 Bath | Sleeps 5

River Road Retreat - Chestertown, NY

$248 avg / night
4.5 (2)
Pine's Way Camp
4 Bed | 2 Bath | Sleeps 6

Pine's Way Camp - Chestertown, NY

$222 avg / night
4.38 (32)

View 8 more homes

Recent Chestertown vacation rental reviews

We booked this home for a girls weekend and couldn’t have had more of a good time. This home is beautiful. You can tell the family that owns this home puts so much love and care into making it feel special. It’s was so clean and put together. I have zero complaints. Plan to book this same home again next year for another weekend.
Lindsay P. | Nov 2024
We stayed here last weekend. The home was well stocked with everything you could possible need and very clean. I went with a group of 4 other adults, but will definitely be booking again to bring my family and grandkids.
Anna Mae A. | Oct 2024
We enjoyed the location. It was easy to get to area adventures.
Noreen P. | Oct 2024
Chestertown Frequently Asked Questions

Yes, 14 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. 54 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.