Vacation rentals in Chestertown

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.

4.96 out of 5 average rating, 115 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!

The front view of a spacious, single-story house is presented, featuring a welcoming porch with steps leading to the entrance. Large windows on either side frame the doorway, surrounded by lush green grass and trees in the background, indicating a peaceful, natural setting.

5.0 out of 5 average rating, 61 reviews

The Hayes Homestead

Our family has enjoyed this home in the Adirondacks for decades. We are opening the doors to share this little gem with others and allow you to experience the peacefulness of the Homestead, nestled in the heart of the Adirondack Mountains. Located only 20 minutes from Lake George, Gore Mountain, and Schroon Lake, an hour from Saratoga Springs, with easy access to local snowmobile trails. Enjoy coffee on the large front porch and relax with the whole family at this peaceful place to stay.

4.95 out of 5 average rating, 103 reviews

An open floor plan is showcased, featuring rustic wooden beams and warm tones. A comfortable seating area with a wooden couch and area rug leads to a staircase. The kitchen is visible in the background, adjacent to a dining space with a television and natural light from large windows.

Barn in Chestertown

Adirondack Base Camp by Loon Lake and Gore Mt.!

This unique, rustic and family-friendly ADK base camp will help you make great memories! This 1900 built, renovated barn is on 2.4 acres in walking distance to Loon Lake, 2 minute drive to the public beach and boat launch and a mere 20 minutes to Gore Ski Mountain! With trail heads right up the street, you can hike, bike, fish, hunt, ski, snowmobile, snowshoe, raft, kayak and tube, explore the region, R&R or sled on Dynamite Hill! 5 minutes off route 87, and 20 minutes from Lake George.

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.

4.96 out of 5 average rating, 271 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.

4.96 out of 5 average rating, 280 reviews

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

Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+

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, primary bedroom, loft w/ 2 sofa beds, desk, big lawn, grill, ski chair + LVL 2 EV charger. Fast Wi-Fi • Self check-in • Please read house rules!

Superhost

A spacious deck features a hot tub surrounded by lush greenery. Two comfortable seating areas, including two round chairs and a side table, offer a relaxing space. The backyard reveals a picturesque lawn, creating a serene outdoor atmosphere for enjoyment.

4.9 out of 5 average rating, 125 reviews

Adirondack 🏠 near Gore Mt, North Creek, Loon lake.

Welcome to Loon Run Lodge that is located in the Adirondack mountains of upstate New York, ready to be your place to relax and enjoy skiing, snowshoeing, cross country skiing, snowmobiling, hiking, horseback riding, kayaking, boating, and swimming. This property only 15 min from Gore Mountain ski resort, few minutes to Adirondack Snowmobile Tour, loon lake beach, Loon Lake Marina, local restaurants and stores. Only 20 min to Lake George, Bolton Landing and 25 min to Lake George Village.

5.0 out of 5 average rating, 189 reviews

A private back deck is featured with a round table surrounded by four chairs, all under a large orange and red striped umbrella. A grill is positioned nearby, with lush green trees providing a natural backdrop.

Home in Adirondack

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.

4.98 out of 5 average rating, 175 reviews

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

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.

5.0 out of 5 average rating, 280 reviews

A tranquil lake scene is depicted, featuring a clear blue sky reflecting on still waters. Lush greenery surrounds the shore, and the vibrant foliage can be observed on the hillside. A cozy red cottage is subtly mirrored in the lake's surface, enhancing the serene ambiance.

Cottage in Adirondack

Water's Edge at Beaver Pond

Like being on a boathouse, this unique custom cottage/camp embraces the spirit of Adirondack lakehouse living... with a breathtaking view from every room! Perched on the shore of private Beaver Pond, this pristine lake offers great recreational activities (canoe/ kayak/ paddleboard/ swimming/ fishing). Inside the cottage, this home is designed with every detail carefully selected, and all modern amenities included! Cozy, comfortable and well-appointed... a perfect vacation location!

4.93 out of 5 average rating, 57 reviews

Cottage in Chestertown

Private Loon Lake property, cozy cabin on 3 Acres

Relax and recharge at this peaceful 4 season cottage right on Loon Lake. A new boat dock is here. Comes with 2 adult and one child’s kayak and a paddle boat on your own private cove. Enjoy a fire on the lake or up by the cottage. A great place for a restful retreat or the staging area for your great Adirondack adventures. Lose yourself in Nature with local hikes for all abilities, water sports, leaf peeping from your screened in porch, and winter sports abound. New kitchen in 2026.

The exterior view of the North Pine Lodge showcases a two-story wooden structure surrounded by lush greenery. A spacious deck lined with red chairs invites relaxation, while tall trees provide natural shade and a sense of seclusion.

4.94 out of 5 average rating, 99 reviews

Family friendly Adirondack dream, no cleaning fee!

The North Pine Lodge accommodates families of any size w/ 3 bedrooms and 2 full baths. Each of the 2 upstairs bedrooms feature a queen bed, as well as an elevated sleeping loft complete with twin mattress. The master boasts a king size bed, and murphy style fold down bunks! The finished daylight basement family room features a queen size sleeper sofa. All just minutes to Gore Mtn, Lake George village, and countless other ADK activities, come explore!