Vacation rentals in Chestertown

Adirondacks Summer Escape | Hot tub Grill&Firepit

Welcome to our charming log cabin across the street from Schroon River! This 2 bed 2 bath cabin is located about 15 minutes from Lake George! Indulge in the luxury log cabin lifestyle without compromising on convenience! ✔ Sleeps up to 6 guests ✔ 2 bedrooms & 2 full baths ✔ West Elm sofa converts into Queen bed ✔ High speed WiFi ✔ AC units in bedrooms from June - Sept ONLY ✔ Brand NEW hot tub ✔ Brand NEW Generator ✔ Smart TV w/ Roku - pick up where you left off on your own streaming services

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

Bolton Landing - Cozy Adirondack Cabin Home & Ski

Small Adirondack cabin with a loft type sleeping area. One queen bed and a full size futon. Can easily host 2 adults and 2 children. Two couples are possible but limited privacy. Renovated cabin in Bolton Landing. Private setting with short walk to the Pinnacle trail head, 5 minute quick drive into town for groceries, public town beach, boat launch, Sagamore Resort, public beaches, restaurants, brewery, and shops. Gore ski area (40 minute drive. Dog pets are on an exception basis.

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.

Cabin on a Babbling Brook in the Adirondacks

Tucked away off the beaten path, this Adirondack getaway invites you to reset, recharge, and reconnect with nature. 6 private acres on 247 ft of water frontage on the babbling Trout Brook. 5 mi away from Schroon Lake public beach, Tops grocery store, Steps to Hoffman notch 38,000+ acres of state land) from the property. Whether you’re here for hiking the High Peaks, fishing, paddling, or simply escaping the noise, this is the perfect base camp for nature lovers and outdoor enthusiast.

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!

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)

Pearl of the Mountain

The Beebe Farm was started in 1921 by Fred and Pearl Beebe. There are now four generations of Beebe's who have farmed this land. Over time these spectacular views have been created by hard work and devotion to agriculture. We offer this rental for you to relax and enjoy the breathtaking panorama of Lake Champlain, the Green Mountains of Vermont, and the eastern slopes of the Adirondacks. Many activities and attractions can be found close by!