Chestertown Vacation Rentals

Compare 13 vacation rentals.
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Make Chestertown your next getaway

Explore Our Chestertown Vacation Rentals

Top Chestertown property types

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House rentals

View 10 House rentals
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Cottages

View 2 Cottages
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Farmhouses

View 1 Farmhouses

Popular amenities for Chestertown vacation rentals

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

Whit's End - Chestertown, NY

$201 avg / night
(excludes fees and taxes)
4.83 (40)
Loon Lodge
5 Bedroom | 3 Bath | Sleeps 10

Loon Lodge - Chestertown, NY

$440 avg / night
(excludes fees and taxes)
4.65 (63)
Pine's Way Camp
4 Bedroom | 2 Bath | Sleeps 6

Pine's Way Camp - Chestertown, NY

$176 avg / night
(excludes fees and taxes)
4.32 (38)
Basic Adirondack Camp
3 Bedroom | 1 Bath | Sleeps 6

Basic Adirondack Camp - Chestertown, NY

$200 avg / night
(excludes fees and taxes)
4.04 (23)
Hillcrest Acres Retreat
3 Bedroom | 2 Bath | Sleeps 6

Hillcrest Acres Retreat - Chestertown, NY

$257 avg / night
(excludes fees and taxes)

View 8 more homes

Recent Chestertown guest reviews

Loved the spacious home with plenty to entertain kids of all ages. Kitchen was stocked for cooking, minus a few necessities (salt, coffee, coffee filters).
Kathryn H. | Jan 2026
Absolutely love everything about this place. Just please don't rent it when I do! Lol
Tracy G. | Jan 2026
The house was well kept. We enjoyed our stay. The lake was frozen and could be seen inside the house next to the fireplace. I went walking onto the lake with traction and had much fun. We will return if we should visit Chestertown again. Though hair dryer, wifi and water kettle can use improvements.
Rita S. | Dec 2025
Chestertown vacation rental FAQ

Yes. 41 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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Chestertown, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons 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.