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!

2 bdrm ADK cabin 10 mins to GORE MTN

The "Mellow Moose" cabin is a quiet and peaceful retreat tucked in the woods. Spend the day exploring the region or just simply relaxing 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 a way to explore Schroon lake, Brant lake or Lake George. (Roughly 30mins)

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.

Chestertown Charm: minutes to Loon Lake

Bring the whole family to this charming four-season home with lots of room for fun. Two queen bdrms, a great room with futon and a single bed and 2 and 1/2 renovated baths, fully stocked kitchen and workspace w/ hi-speed internet. Stroll to the local ice cream parlor. Enjoying local hiking, boating, or swimming at nearby Loon Lake and Brant Lake. Ski at Gore- 25 mins. Visit Lake George- 25 mins, Lake Placid- 75 mins. Located on snowmobile trail! Bring own boat or snowmobile. Room to park.

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.

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.

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 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.

Pond Farmhouse: Private Hot Tub, Fire Pit, Town

Discover your inviting Adirondack retreat in Chestertown, NY. This beautifully restored 1860 farmhouse on Faxon Pond offers private waterfront access, a dock, canoe, luxurious hot tub, and fire pit. This 3-bedroom, pet-friendly home blends relaxation with year-round adventure. Enjoy modern comforts, a fully equipped kitchen, and easy access to local attractions. Comfortably accommodates up to 8 guests with additional sofa beds, providing a tranquil escape in the heart of the Adirondacks.

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.

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.

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!