Chestertown Vacation Rentals

Compare 13 vacation rentals.
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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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Popular amenities for Chestertown vacation rentals

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

Loon Lodge - Chestertown, NY

$400 avg / night
4.59 (51)
Pine's Way Camp
4 Bedroom | 2 Bath | Sleeps 6

Pine's Way Camp - Chestertown, NY

$187 avg / night
4.38 (32)
Whit's End
4 Bedroom | 3.5 Bath | Sleeps 8

Whit's End - Chestertown, NY

$370 avg / night
4.82 (33)
Retreat on the Pond
3 Bedroom | 1 Bath | Sleeps 8 (6 Adults Max)

Retreat on the Pond - Chestertown, NY

$249 avg / night
4.8 (10)
Lakeside Vibes
3 Bedroom | 1 Bath | Sleeps 6 (4 Adults Max)

Lakeside Vibes - Chestertown, NY

$372 avg / night
4.41 (17)

View 8 more homes

Recent Chestertown guest reviews

The house was great for a winter ski trip. It’s 15-20 min from Gore. Easy drive. We were there during a snow storm and the driveway was plowed. The house was beautiful and perfect for two families. The kids loved the ping pong table and playing in both the loft and basement. Check in and check out was very easy. We would definitely come back!
Erica O. | Feb 2025
We spent President´s weekend for a ski trip. The house is very nice and very clean. Photos are very accurate. We had a great time!
Ana F. | Feb 2025
This house was warm and inviting and spotless. Plenty of room to spread out and relax. Clearly was renovated and looks amazing. Beds comfortable and loved that the TV was in a different living area so we weren’t distracted by that. Only 20min to Gore Mtn. Would love to come back in the summer ! Beautiful lake views even in the winter.
Christine S. | Jan 2025
Chestertown vacation rental FAQ

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. 51 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.