Vacation rentals in Chestertown

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chestertown

Guests agree: these stays are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Top guest favorite
Three Adirondack chairs are positioned by the riverbank, providing a view of the flowing Hudson River. Leafless trees frame the scene under a clear blue sky, with hints of snow visible along the water's edge, creating a serene ambiance.
Chalet in Warrensburg
4.98 out of 5 average rating, 129 reviews

ADK River Rapture- Warrensburg/Lk George/Gore Mntn

Elegant 3BR/3BaR Waterfront home with river access minutes from Lake George & Gore Mountain...river, lake & ski fun abound! Wraparound deck & floor to ceiling windows offer stunning Hudson River and mountain views from all angles. Open concept main floor has cathedral ceiling, magnificent stone fireplace in Great Room, custom hardwood floors, new granite kitchen & 3 spacious upstair BR's. Master BR offers a private, en suite bath while 2 guest bedrooms share another full bath. Total tranquility!

Top guest favorite
Cabin in Warrensburg
5 out of 5 average rating, 266 reviews

Romantic Christmas Getaway~30 Min to Gore Mountain

*Romantic getaway nestled in the Adirondack Mountains, just 15 minutes to Lake George *Vintage Record Player, Farm Fresh Eggs and pollinator gardens *A dreamy escape into nature where you will wake up and feel like you are still dreaming *This is not just any five star stay step outside we have millions our night sky is breathtaking *We strive for our guests to have nothing less than a five star experience, as you can see by our reviews Chickadee is decorated for Christmas Nov -New Year’s

Guest favorite
The great room features vaulted wood ceilings with exposed beams and large windows allowing natural light. A comfortable blue sectional sofa is situated near a stone fireplace, while a dining area with a wooden table is visible in the background. The kitchen is defined by light wood cabinetry.
Home in Chestertown
4.97 out of 5 average rating, 103 reviews

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

Welcome to Jackson's Lodge! Looking for an Adirondack escape for your family and friends in any season? Nestled in a private, 4 acre park like setting in the Southeast ADKs, this cozy mid century modern cabin will show you what upstate NY living is all about. After exploring the best the ADKs have to offer, come soak in the hot tub, unwind in the cedar screened-in porch, or pull up a chair to the natural stone fire pit. Roast some 'smores, take in the night sky, and let your stress melt away!

Top guest favorite
The exterior of a vibrant red barn is shown, featuring a decorative quilt square on the wall. The sky is painted in shades of purple and pink, with clouds softly contrasting the structure. Lush green grass surrounds the base, contributing to the serene environment.
Barn in Chestertown
4.96 out of 5 average rating, 247 reviews

Cozy Red Barn Retreat | Hot Tub, Large Lawn

Relax in this cozy red barn! Rustic charm meets modern luxury. 1 min off I‑87 1 min to Schroon River 2 mins to Loon Lake 5 mins to Brant Lake 25 mins to Gore Mtn + Lake George Near tons of hikes, lakes & swimming holes +close to town! Unwind in the hot tub, cook in the full kitchen, and gather by the fire pit. Features: dining area, big shower, private bedroom, loft w/ 2 sofa beds, desk, big lawn, BBQ, ski chair swing + LVL 2 EV charger. Fast Wi-Fi • Self check-in • Please read house rules

Top guest favorite
Camper/RV in Johnsburg
4.97 out of 5 average rating, 102 reviews

Happy Camper!

***Guests must walk 420ft from the parking spot through the woods to reach the RV. There is a cart / sled for you to use. *In WINTER* The main trail will not be plowed. You must snow shoe or sled through the woods. Private, year-round, 4 person Hot tub! 420 Friendly! There may be beer in the fridge. Over the years guests have started a "Take a Beer Leave a Beer" tradition. Pets Welcome! CHECK IN 4PM - 8PM Wood & Eggs for sale on site! $10 Large wood bundles $5 dozen free range eggs

Top guest favorite
A spacious living area features a cozy sofa and wooden furniture, complemented by a glass coffee table. Natural light illuminates the room through large windows, while soft drapes provide privacy. A warm wooden ceiling enhances the inviting ambiance.
Home in Chestertown
4.95 out of 5 average rating, 249 reviews

Adirondack Lake House

Adirondack beauty all year! Fully furnished home has lovely great room, fireplace , two bedrooms, one bath, basement family room, large deck, outdoor fire pit, screened porch with lake glimpse, limited air conditioning, rights to private lake, kayaks, canoes, w/d, fire pit with wood, in quiet wooded setting. Central location. This is NOT a lakefront property. It comes with lake access and is located across the street from the lake. Please see complete listing for accurate information.

Top guest favorite
A cozy guest house is visible, surrounded by snow-covered trees and a white landscape. Fresh snow blankets the ground and the home's roof, while a clear path leads to the entrance. The exterior features warm orange siding, providing a contrast to the winter scene.
Home in Adirondack
5 out of 5 average rating, 170 reviews

Adirondack Owl's Nest Guest House

Our Adirondack Guest House is centrally located to many nearby attractions the region has to offer. Located on 10 wooded acres, just minutes off Northway I-87. Only 2 miles from Schroon Lake boat launch and Word of Life. Minutes to Brant Lake & Loon Lake. A short drive to beautiful Lake George and nearby Gore Mountain. The area offers: swimming, hiking, bicycling, fishing, golfing, canoeing & kayaking, river tubing, adventure course, rodeos, skiing, snowshoeing, sledding, & snowmobiling.

Top guest favorite
The modern chalet-style home is set among tall trees, featuring a spacious wrap-around deck with outdoor seating. The peaked roof adds a distinct character, while large windows allow natural light to flood the interior. The sandy ground surrounds the lower level, enhancing the natural setting.
Chalet in Chestertown
4.98 out of 5 average rating, 168 reviews

Chalet on Loon Lake (Gore Mt. 20 min.)

Located on beautiful Loon Lake, this modern chalet style home, with private beach and dock, features an open floor plan with 4 bedrooms, 2 full baths and loft. The house is fully furnished and has all the creature comforts. Outdoor amenities include a wrap-around deck and outdoor dining furniture. Enjoy boating, fishing, hiking, skiing and snowmobiling. Located just 30 minutes from Lake George and 20 minutes from Gore Mountain and the North Creek Ski Bowl and cross county trail system.

Top guest favorite
Aerial view of the Owls Nest Log Home, surrounded by dense evergreen trees and rolling hills. A winding river flows nearby, reflecting the clear blue sky. The home's red roof contrasts with the lush green landscape, promoting a sense of seclusion and tranquility.
Home in Warrensburg
4.98 out of 5 average rating, 123 reviews

Lake George | Hot Tub | Firepit | Schroon Lake

Escape this summer or winter to The Owls Nest Log Home! Just steps away from the Schroon River, indulge in fishing, kayaking, canoeing, rafting, skiing, snowboarding, snowmobile and more. Hiking trails are nearby and lakes like Brant Lake, Lake George, and Schroon Lake are just a short drive away. Unwind in the hot tub with a glass of wine while enjoying the serene sounds of the river. Our fully-equipped home is perfect for families or couples looking for an stress-free vacation.

Guest favorite
A cozy seating area is highlighted by a brown leather sofa and a woven basket. A rug lies beneath, creating a comfortable ambiance. The adjoining wall displays the text 'ADK Stay' in a stylish font, adding a welcoming touch. Natural light enhances the space.
Apartment in Schroon Lake
4.91 out of 5 average rating, 160 reviews

ADK Stay

Keep it simple at this peaceful and private apartment in the heaven on earth that is Schroon Lake. We have traveled around the globe, staying in a myriad of vacation rentals. Since then, we've renovated the private apartment attached to our home to accommodate guests and we hope to take our countless stays into consideration to create the best possible guest experience here in the lovely place we call home, the Adirondacks! We hope you'll enjoy our home as much as we do!

Top guest favorite
A bright living room features large windows framed with red-checkered curtains, allowing natural light to fill the space. A cozy couch and a coffee table are placed near a gas fireplace, while a wooden ceiling adds warmth to the design. A view of snow-covered outdoor surroundings is visible through the glass doors.
Cabin in Johnsburg
4.97 out of 5 average rating, 143 reviews

2 bdrm ADK cabin 10 mins to GORE MTN

The "Mellow Moose" cabin is a quiet and peaceful retreat in the woods. Spend the day exploring the region or simply relax in nature. Afternoons are great for reading a book as the sun shines through the large living room windows. Relax on the screened in front porch for a quiet evening and a drink. Or enjoy a campfire and watch the sunset through the trees. Use this as your home base for a ski trip or take a trip to Schroon lake, Brant lake or Lake George. (Roughly 30mins)

Top guest favorite
A modern Scandinavian cabin is showcased, illuminated by soft lighting in the evening. A fire pit is centered in the snow-covered outdoor area, surrounded by wooden seating. The cabin features large glass doors that reveal a cozy interior, harmonizing with the natural surroundings.
Tiny home in North Hudson
4.92 out of 5 average rating, 110 reviews

Private ADK Tiny Home & Hot Tub for Two!

Stay Mountainbound is a Scandinavian- style cabin, tucked away in the Adirondacks. This refined retreat is designed with the modern couple in mind. This is the place for those wanting to get away from it all without sacrificing comfort and style. Privately located between pristine Schroon Lake and Keene Valley and within an hour drive to many high peaks and several world class ski resorts including Whiteface, Gore, and West Mountain.

Popular amenities for Chestertown vacation rentals

Quick stats about vacation rentals in Chestertown

  • Nightly prices starting at

    Chestertown vacation rentals start at G$18,825 GYD per night before taxes and fees

  • Verified guest reviews

    Over 290 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chestertown rentals

  • 4.9 Average rating

    Chestertown stays are highly rated by guests—averaging 4.9 out of 5!

  1. Airbnb
  2. United States
  3. New York
  4. Warren County
  5. Chestertown