Holiday rentals in Chester

Private Spacious Suite near Gore, Peaks, WOL-BI

Come & be rejuvenated at our spacious & peaceful suite located at the south end of Schroon Lake in Pottersville, NY. 25 mins to Gore Mt & 30 mins to hiking the ADK High Peaks. Located on a quiet private road, 2 miles off Northway/87. Perfect for a romantic couples retreat or a small family getaway. In any season, we are surrounded with an abundance of activities & local attractions to enjoy. Lake George is 25 min south & Lake Placid 1 hour north. Come explore the splendor of the Adirondacks!!

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

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.

Gore Mountain Studio Retreat

Relax and refresh in our studio apartment after an exhilarating day on the slopes, whitewater rafting on the Hudson, or a less vigorous pursuit. This cozy hideaway, nestled in timber, feels a little like sleeping in a tree house. Located on a quiet and peaceful road with views of Gore Mountain and the Hudson River, it is 5 minutes to the base of Gore Mountain Ski Area and 3 minutes to downtown North Creek with restaurants and shopping. Your Adirondack adventure starts and ends here!

Lux Cabin in the ADK w/fireplace mins to Gore Mnt.

Come enjoy this wonderful "Lil Log Cabin" with luxuries and privacy for an unforgettable Adirondack escape. With Wifi throughout the 4-acre estate, indoor/outdoor music and 65" 4k TV in the main room. Simply cozy up with a great book by the fire or roast marshmallows after a day of limitless outdoor adventures. With multiple destinations in every direction, we are centrally located near hiking paths, ski mountains, lake George's lively entertainment, Bolton Landing and so much more.

Romantic Getaway at Firefly Mountain

💫 A place made for two… Escape to your own private romantic hideaway in the Adirondacks, tucked among whispering pines and star-filled skies. This cozy cabin was designed for couples who want to slow down, reconnect, and enjoy simple magic together — firelight, quiet mornings, long talks, and late-night stargazing. Pour a glass of wine, curl up together next to the fireplace , and let the world disappear for a while. This is not just any 5 ⭐️stay step outside we have Millions !!

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 skiing (both alpine & nordic), hiking, mountain biking, kayaking, rafting and fishing are all within 15 minutes of our location.

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)

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!

Rustic Tiny Cabin

This tiny, magical, rustic, cabin is situated overlooking a large pond on a private property of 200+ acres. Though the cabin is very small (about 10x12 ft with an upstairs sleeping loft) it is quaint and lovingly made with hand split cedar shingles and locally harvested wood. There is an outhouse and no power/running water, but a 5 gallon cooler of spring-fed drinking water is provided.