Chestertown 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

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Farmhouses

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Browse more vacation rental amenities in Chestertown

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

Popular amenities for Chestertown vacation rentals

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

Loon Lodge - Chestertown, NY

$407 avg / night
(excludes fees and taxes)
4.67 (67)
Pine's Way Camp
4 Bedroom | 2 Bath | Sleeps 6

Pine's Way Camp - Chestertown, NY

$162 avg / night
(excludes fees and taxes)
4.22 (40)
Hillcrest Acres Retreat
3 Bedroom | 2 Bath | Sleeps 6

Hillcrest Acres Retreat - Chestertown, NY

$240 avg / night
(excludes fees and taxes)
2.5 (2)
Edgewater Cabin
1 Bedroom | 2 Bath | Sleeps 2

Edgewater Cabin - Chestertown, NY

$153 avg / night
(excludes fees and taxes)
4.69 (13)
Lakeside Vibes
3 Bedroom | 1 Bath | Sleeps 6 (4 Adults Max)

Lakeside Vibes - Chestertown, NY

$354 avg / night
(excludes fees and taxes)
4.42 (19)

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Recent Chestertown guest reviews

This is a fabulous property. The photos are old and do not reflect the updated bathroom, bedrooms and outdoor areas. We really liked this property. The beds were comfortable. Ample bath and beach towels were provided. The kitchen is relatively well stocked. Pack dish soap and laundry supplies as they were not provided. The outdoor lot is very special. We brought our pickleball equipment and played on the tennis court. There is a double seater tree swing, a new children’s swing-set and a secluded area for campfires in a huge hearth. We spent a lot of time enjoying the front porch and gazebo. Loon Lake is a busy lake. There were many motorboats, water skiers and tubers. It made it difficult to use our kayaks because of the heavy traffic. We were also hesitant to swim because the boats come close to the dock. However, I have no hesitancy to recommend The Lakeside White House and Vacasa was very responsive to my inquiries.
Jeanne E. | Jul 2026
The lake life during our weeks stay was amazing. The home was big and comfortable, the pics were great, the real experience was even better. Loved the walk in lake and dock for swimming fun. The canoe and kayaks were a bonus. I will rent this home again!
Sonja C. | Jul 2026
Comfortable beds. Gas grille right on deck. Wood campfire and smores. Kayaking and canoeing.
John S. | Jun 2026
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.

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   |   Athol   |   Diamond Point   |   Schroon Lake   |   Minerva   |   Huletts Landing   |   Kattskill Bay   |   Silver Bay   |   Lake George   |   Severance   |   Hague   |   Clemons   |   Queensbury   |   Putnam Station   |   Fort Ann   |   Glens Falls North   |   Hadley   |   Ticonderoga   |   Glens Falls   |   Indian Lake   |   Fair Haven   |   Corinth   |   Fort Edward   |   Newcomb   |   Shoreham   |   Poultney   |   Bomoseen   |   New York
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