Holiday rentals in Chestertown

Quaint Adirondack Condo

This cozy Adirondack condo on Tripp Lake boasts 1 tranquil loft bedroom with a king bed. The living room can accommodate up to 3 extra guests. Amenities available on grounds include a private beach, bocce ball court, tennis courts, and golf course. Don’t hesitate to explore off the property for some great hiking, swimming, and views of the surrounding area. Take a quick drive to Lake George (~20 min) for some summer fun, or venture to Gore Mountain during the winter for some excellent skiing!

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.

Bearpine Cottage

Beautiful 2 bedroom Cottage with living room, kitchen , 1 bath - Ideal for small family up to 6 . Perfect for 4 people. (2 queen beds and a pull out queen in living room ) -Large screen porch -Large grassy lawn -Plenty of free parking -Wi-Fi -TV -The river is across the street. -7 minutes to Main street of Warresburg - 12 minutes to Main Street Lake George -10 minutes to Gore ski Mountain -minutes from ADK hiking trails all over - 5 minutes to Cronins golf Course on the river -Fire pit

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!

Big Bear Lodge w/ Hot Tub and Sauna

Enjoy a complimentary Sauna and outdoor fire start on your first night at this historic Log Lodge. This home is filled with modern amenities, such as a 6 burner gas stove, 65 inch TV and more. This home has cathedral ceilings, a working wood stove and a breathtaking chimney. 4 kayaks provided as well as 5 fishing poles. Perfect for your next vacation! Local Attractions: 40 min to Keene Valley and the high peaks. 30 min to Lake George 15 min to Gore Ski Mountan 4 min to Loon Lake Beach

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!