Chestertown Vacation Rentals

Compare 15 vacation rentals.
USA > New York > Chestertown

Make Chestertown your next getaway

Explore Our Chestertown Vacation Rentals

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


House rentals

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View 2 Cottages

Chateau rentals

View 1 Chateau rentals

Chestertown vacation rentals for every getaway

Dog-friendly Hot tub Internet
Loon Lodge
5 Bedroom | 3 Bath | Sleeps 10

Loon Lodge - Chestertown, NY

$379 avg / night
Whit's End
4 Bedroom | 3.5 Bath | Sleeps 8

Whit's End - Chestertown, NY

$309 avg / night
Retreat on the Pond
3 Bedroom | 1 Bath | Sleeps 8 (6 Adults Max)

Retreat on the Pond - Chestertown, NY

$225 avg / night
River Road Retreat
3 Bedroom | 1 Bath | Sleeps 6

River Road Retreat - Chestertown, NY

$173 avg / night
The Stock Farm
3 Bedroom | 3 Bath | Sleeps 7

The Stock Farm - Chestertown, NY

$267 avg / night

View 10 more homes

Recent Chestertown vacation rental reviews

Winter wonderland of frozen lake
Chester S. | Jan 2024
a very well located, comfortable and very private place, the house is beautiful, very clean when checking in, and very cozy, it has nearby places to ski and enjoy the snow in winter, there are gas stations nearby, a Stewart store, and in the center of town, which is only 5 minutes away, there are many shops to shop,
Jesus M. | Jan 2024
We had a wonderful time staying at this property during our Gore Mountain ski vacation. The decorations were lovely. The kitchen was very well stocked with tools and pans and it was a pleasure to prepare meals there. The furniture was comfortable and cozy. Thank you for creating such a beautiful place and letting us stay there during our vacation.
Landon R. | Jan 2024
Chestertown vacation rental FAQ

Yes, 16 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. 58 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.