Vacation rentals in Chestertown

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 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.

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.

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.

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!

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.

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.

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.

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!

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.

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!

House in the Adirondacks, 15 min from Gore!

This is a beautiful house that sits facing Loon Lake! Amazing views from the living room with balcony and also the master bedroom. Has a very large boat dock across the road where you can fish from all day and enjoy dinner from while watching the sunset. See the beautiful fall foliage on Kipp mountain directly from the house! Great place for skiers to stay as Gore mountain is only 15 minutes away. Also fantastic for ice fishing on Loon Lake!