Chestertown Vacation Rentals

Compare 616 vacation rentals with savings up to 30% off this summer.
USA > New York > Chestertown

Make Chestertown your next getaway

Explore Our Chestertown Vacation Rentals

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


House rentals

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Chateau rentals

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View 1 Cottages

Chestertown vacation rentals for every getaway

Dog-friendly Hot tub Internet
Riverside Bliss
3 Bed | 2 Bath | Sleeps 7

Riverside Bliss - Chestertown, NY

$407 avg / night
Lakeside Vibes
3 Bed | 1 Bath | Sleeps 6 (4 Adults Max)

Lakeside Vibes - Chestertown, NY

$312 avg / night
Whit's End
4 Bed | 3.5 Bath | Sleeps 8

Whit's End - Chestertown, NY

$436 avg / night
Loon Lookout Chalet
4 Bed | 3 Bath | Sleeps 8

Loon Lookout Chalet - Chestertown, NY

$422 avg / night
Loon Lodge
5 Bed | 3 Bath | Sleeps 10

Loon Lodge - Chestertown, NY

$540 avg / night

View 8 more homes

Recent Chestertown vacation rental reviews

The privacy, the view of the lake, and hearing the loons. The owners clearly have a great sense of the value of the outdoors and the peace it brings.
Robert P. | Apr 2023
The house was spacious, very clean, perfectly located and convenient for a ski weekend. Would definitely stay again!
Donna H. | Mar 2023
We came here for a little ski trip. The house was perfect. Clean, nicely decorated and warm and cozy! Enough space for kids and adults. It was only 16 mins to Gore mountain . We definitely will be coming back next year! Thanks again Paul and Eileen Whitman!!
Nicole C. | Mar 2023
Chestertown Frequently Asked Questions

Yes, 13 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. 48 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.