Chestertown Vacation Rentals

Compare 12 vacation rentals.
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Make Chestertown your next getaway

Explore Our Chestertown Vacation Rentals

Explore Chestertown house rentals, cottages, farmhouses, and more

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House rentals

View 9 House rentals
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Cottages

View 2 Cottages
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Farmhouses

View 1 Farmhouses

Explore more vacation rental amenities in Chestertown

Electric vehicle charger | Lake view | Lakefront | Riverfront | Water view | Waterfront | A/C | Fireplace | Washer/dryer | Balcony

Chestertown vacation rentals for every getaway

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

Loon Lodge - Chestertown, NY

$621 avg / night
(excludes fees and taxes)
4.64 (61)
Whit's End
4 Bed | 3.5 Bath | Sleeps 8

Whit's End - Chestertown, NY

$285 avg / night
(excludes fees and taxes)
4.82 (39)
Pine's Way Camp
4 Bed | 2 Bath | Sleeps 6

Pine's Way Camp - Chestertown, NY

$272 avg / night
(excludes fees and taxes)
4.32 (38)
Basic Adirondack Camp
3 Bed | 1 Bath | Sleeps 6

Basic Adirondack Camp - Chestertown, NY

$269 avg / night
(excludes fees and taxes)
4.04 (23)
Hudson Riverside Cottage
2 Bed | 1 Bath | Sleeps 4

Hudson Riverside Cottage - Chestertown, NY

$248 avg / night
(excludes fees and taxes)
4.75 (4)

View 7 more homes

Recent Chestertown vacation rental reviews

This house was perfect for our thirteenth womens weekend! Finding a house for nine adult women is hard, and this house completely fit the bill. It had more than enough beds, and no bunk beds which is perfect for us! The open floor plan is exactly what we like. Plenty of seating both for dinning and relaxing. Showers were awesome. The lower level was lovely, not dank or musty like many we have experienced. The view is spectacular. We went off season but loved being on the water. We immediately wanted to book for next year but alas, it’s not available. We will keep an eye on this place though, maybe year fifteen.
Jennifer B. | Nov 2025
This home is very well stocked and comfortable spaces for all! We loved it!
Dawn Y. | Oct 2025
We loved how much the cabin felt like home. My family and I were able to immediately feel comfortable. It had some flaws but nothing that would take away from the relaxing experience we were able to have.
Tabetha R. | Oct 2025
Chestertown Frequently Asked Questions

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 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.

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