Holiday rentals in Chestertown

Secluded and Cozy Townhome at Tripp Lake

You will find a great stay during any season at this townhome located in the Southern Adirondacks. We are central to many outdoor activities including Summer features include a short 15 minute drive to Lake George, 5-20 minutes from white water rafting, tubing, hiking, cruise boats, powerboat rentals and the Great Escape. Winter activities include downhill skiing with a short 20 minute drive to Gore Mountain. Other things to do include hiking, historical attractions, nature trails and shopping.

Family · Location · Access

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!

Location · Family · Indoor spaces

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)

Location · Value · Nearby

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!

Location · Family · Condition

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.

Value · Location · Outdoor spaces

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.

Value · Location · Hospitality

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.

Value · Family · Hot tub

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!

Location · Family · TV

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.

Value · Family · Condition

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.

Location · Family · Sleep quality

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!

Value · Family · Sleep quality

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!

Value · Family · Quiet