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
Loon Lodge
5 Bedroom | 3 Bath | Sleeps 10

Loon Lodge - Chestertown, NY

$391 avg / night
(excludes fees and taxes)
4.66 (65)
Pine's Way Camp
4 Bedroom | 2 Bath | Sleeps 6

Pine's Way Camp - Chestertown, NY

$188 avg / night
(excludes fees and taxes)
4.23 (39)
Hillcrest Acres Retreat
3 Bedroom | 2 Bath | Sleeps 6

Hillcrest Acres Retreat - Chestertown, NY

$275 avg / night
(excludes fees and taxes)
Lakeside Vibes
3 Bedroom | 1 Bath | Sleeps 6 (4 Adults Max)

Lakeside Vibes - Chestertown, NY

$378 avg / night
(excludes fees and taxes)
4.42 (19)
Edgewater Cabin
1 Bedroom | 2 Bath | Sleeps 2

Edgewater Cabin - Chestertown, NY

$158 avg / night
(excludes fees and taxes)
4.69 (13)

View 8 more homes

Browse more vacation rental amenities in Chestertown

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

Recent Chestertown guest reviews

Ithe house was amazing very cozy great and well kept. Id reccomend staying to anyone. Only real issue we ahd was with proeprty management. Id fire this property manager and get another one. Was a hassle to get in 30 minute delay on hold whily my identy was verified and signed docs. also when we cxheck out the cleaners showed up early and sat in teh driveway waiting for us to leave. This is a bit pushy in my opinion. We left on time not late but felt rushed
Don H. | Mar 2026
Great location,right by the lake and close to ski lifts. Open inside space give us great time to relax with our family and friends. Really welcoming and beautiful stay.
Maria G. | Mar 2026
The house was perfect for a group of 7 guys for a ski weekend. Close to Gore Mountain. Also close to Lake George for some night life. The view of the lake was beautiful
craig v. | Feb 2026
Chestertown vacation rental FAQ

Yes. 42 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.

Nearby destinations

Upstate New York   |   Adirondacks   |   Gore Mountain   |   Lake George   |   Loon Lake, NY   |   Friends Lake, NY   |   Brant Lake   |   Wevertown   |   Adirondack   |   Bolton Landing   |   Johnsburg   |   Bolton   |   Olmstedville   |   Thurman   |   North Creek   |   Warrensburg   |   Diamond Point   |   Schroon Lake   |   Minerva   |   Kattskill Bay   |   Silver Bay   |   Lake George   |   Hague   |   Queensbury   |   Fort Ann   |   Glens Falls   |   Indian Lake   |   Fair Haven   |   Shoreham   |   Poultney   |   Bomoseen   |   New York
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