Vacation rentals in Chestertown

Lakeside with direct water access & amazing views

La Bella Loona - A beautiful 1 bd cottage located directly on Schroon lake. Amazing mountain and lake views from every window. 50' of direct water access with small sandy beach, outdoor firepit and grill, and multiple hang out spots. The cottage is newly built and furnished, has an indoor fireplace, central AC, fully stocked kitchen, and screened in room overlooking the lake. There are 2 kayaks available for use. Be assured everything is provided to make your stay as comfortable as possible.

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!

Bring Your Dog | River Dock + Fire Table

Your dog wants a relaxing getaway… you can come too! Welcome to Pine & Paw, an Adirondack escape designed for dogs and their people. No pet fee-dogs are family. Access private dock on Schroon River across the street, trails nearby, it’s where muddy paws and lazy days are part of the plan. Launch a kayak, toss a stick, or grill while your pup explores the fenced area. Fully stocked kitchen, peaceful office w/ high-speed WiFi, and a Cali king bed - because your dog called dibs on the middle.

Amazing Adirondack Lodge/Cabin-Crystal Lake

Amazingly appointed Adirondack 3 Bedroom Ski Lodge/Cabin located 15 minutes from Gore Mountain, in Crystal Lake Homeowners Association. Although the property is minutes away from the Gondola at Gore, if you want venture out and mix it up, you are close to West Mountain and about and hour from Lake Placid (Whiteface) and Killington, VT, when you stay at this centrally-located paradise. If cross country skiing and snowmobiling are your preference, there are dozens of local trails to explore!

Chestertown Charm close to Gore Mt. Come ski!

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!

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!

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!

Rustic Adirondack Studio Apartment

Come and enjoy the Adirondacks for an overnight stay or a couple of days. Enjoy our lakefront with access to swimming, kayaking and paddle boarding or just kick back at the dock and enjoy your coffee or other beverage. We are located on Loon Lake outside of Chestertown, NY. Access to many hiking trails is only a short drive away. So come visit and enjoy yourself. We look forward to meeting you!