Chestertown Vacation Rentals

Compare 13 vacation rentals.
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

$399 avg / night
4.58 (50)
Pine's Way Camp
4 Bedroom | 2 Bath | Sleeps 6

Pine's Way Camp - Chestertown, NY

$190 avg / night
4.38 (32)
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)
Whit's End
4 Bedroom | 3.5 Bath | Sleeps 8

Whit's End - Chestertown, NY

$371 avg / night
4.84 (32)
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

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
Loved everything from the view to the coffee maker at this place..
Tracy G. | Jan 2025
This property was perfectly located only 20 mins from Gore Mtn, as a ski destination. It was very clean and inviting when we got there. Good space for everyone. Pros we liked: Great water pressure for a hot shower after skiing! Wonderful lake views Loved the gas fireplace Cons(these are more constructive than all negative) There were no basic cooking spices or even salt in the house. We could have brought with us if we had known. Salt/pepper/garlic and onion powder/cinnamon, and maybe some cooking spray would be a good addition. The basement had a damp/musty smell and could benefit from a dehumidifier running at all times. Better lighting at the street level would help to find the property at night. It is VERY dark on these roads. Thanks for a great stay!
Heather L. | 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. 52 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.