Vacation rentals in Chestertown

A Cozy Creekside Getaway minutes from Gore Mtn.

This quiet getaway is perfect for the family or a small group of friends. This two bedroom, two full bath home is situated on a quiet dirt road right in the heart of the Adirondacks and is perfect for the outdoor enthusiast. It offers easy access to the High Peaks and is just 5 miles from both Gore Mtn. and The Revolution Rail. Opportunities such as hiking, mountain biking, kayaking, rafting and fishing are all within 15 minutes of our location. SEASONAL DISCOUNTS AVAILABLE! Please inquire.

ADK River Rapture- Warrensburg/Lk George/Gore Mntn

Elegant 3BR/3BaR Waterfront home with river access minutes from Lake George & Gore Mountain...river, lake & ski fun abound! Wraparound deck & floor to ceiling windows offer stunning Hudson River and mountain views from all angles. Open concept main floor has cathedral ceiling, magnificent stone fireplace in Great Room, custom hardwood floors, new granite kitchen & 3 spacious upstair BR's. Master BR offers a private, en suite bath while 2 guest bedrooms share another full bath. Total tranquility!

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!

Cozy Red Barn Retreat | Hot Tub, Large Lawn

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, private bedroom, loft w/ 2 sofa beds, desk, big lawn, BBQ, ski chair swing + LVL 2 EV charger. Fast Wi-Fi • Self check-in • Please read house rules

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

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.

The Owl's Nest Tiny Home (Pet Friendly)

Welcome to The Owl’s Nest! We are a newly renovated 380 sq foot tiny home located near all the Adirondack’s has to offer. 🦉 Enjoy all modern amenities while embracing days full of nearby nature and exploring. Plenty of hiking, activities, and restaurants within a 10-30 minute drive. Come back after a long day to watch movies, grill dinner, and enjoy time in our large private backyard or screened in porch. *NOTE. We are located on a walkable residential street, location is not remote*

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.

Lake George | Hot Tub | Firepit | Schroon Lake

Escape this summer or winter to The Owls Nest Log Home! Just steps away from the Schroon River, indulge in fishing, kayaking, canoeing, rafting, skiing, snowboarding, snowmobile and more. Hiking trails are nearby and lakes like Brant Lake, Lake George, and Schroon Lake are just a short drive away. Unwind in the hot tub with a glass of wine while enjoying the serene sounds of the river. Our fully-equipped home is perfect for families or couples looking for an stress-free vacation.

ADK Stay

Keep it simple at this peaceful and private apartment in the heaven on earth that is Schroon Lake. We have traveled around the globe, staying in a myriad of vacation rentals. Since then, we've renovated the private apartment attached to our home to accommodate guests and we hope to take our countless stays into consideration to create the best possible guest experience here in the lovely place we call home, the Adirondacks! We hope you'll enjoy our home as much as we do!

2 bdrm ADK cabin 10 mins to GORE MTN

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

Adirondack Cozy Cabins - Deer Cabin

Just 15 minutes to Lake George! We are located just minutes from outlet shopping, multiple hiking trails, Gore Mountain skiing, Lake George Village and much more. Traveling with friends? We have a total of 3 cabins. Please take a look at my profile to view the Moose and Bear Cabins. This home does not have an EV charging station nor does it allow vehicle charging. There are multiple charging options within 15 minutes of the cabin.