Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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Top guest favourite
Three Adirondack chairs are positioned by the riverbank, providing a view of the flowing Hudson River. Leafless trees frame the scene under a clear blue sky, with hints of snow visible along the water's edge, creating a serene ambiance.
Chalet in Warrensburg
4.98 out of 5 average rating, 131 reviews

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!

Top guest favourite
The exterior of a vibrant red barn is shown, featuring a decorative quilt square on the wall. The sky is painted in shades of purple and pink, with clouds softly contrasting the structure. Lush green grass surrounds the base, contributing to the serene environment.
Barn in Chestertown
4.96 out of 5 average rating, 247 reviews

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

Top guest favourite
A spacious living area features a cozy sofa and wooden furniture, complemented by a glass coffee table. Natural light illuminates the room through large windows, while soft drapes provide privacy. A warm wooden ceiling enhances the inviting ambiance.
Home in Chestertown
4.95 out of 5 average rating, 250 reviews

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.

Top guest favourite
A cozy guest house is visible, surrounded by snow-covered trees and a white landscape. Fresh snow blankets the ground and the home's roof, while a clear path leads to the entrance. The exterior features warm orange siding, providing a contrast to the winter scene.
Home in Adirondack
5 out of 5 average rating, 171 reviews

Adirondack Owl's Nest Guest House

Our Adirondack Guest House is centrally located to many nearby attractions the region has to offer. Located on 10 wooded acres, just minutes off Northway I-87. Only 2 miles from Schroon Lake boat launch and Word of Life. Minutes to Brant Lake & Loon Lake. A short drive to beautiful Lake George and nearby Gore Mountain. The area offers: swimming, hiking, bicycling, fishing, golfing, canoeing & kayaking, river tubing, adventure course, rodeos, skiing, snowshoeing, sledding, & snowmobiling.

Top guest favourite
A studio apartment with a sloped ceiling features a cozy sleeping area with a patterned quilted bedspread. A kitchenette is visible in the background, with wooden cabinets and a white refrigerator. A small dining area with two chairs is situated near the window, allowing for natural light.
Loft in North Creek
5 out of 5 average rating, 132 reviews

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!

Top guest favourite
A cozy great room is furnished with a spacious gray sectional sofa, two white chairs, and a round black coffee table. A large TV is mounted on the wooden wall, complemented by a decorative shelf filled with books. Natural light enters through multiple windows, accentuating the wood paneling.
Cabin in North Creek
4.98 out of 5 average rating, 100 reviews

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.

Top guest favourite
A quiet outdoor setting features two plastic chairs placed near a gathering of firewood, which is arranged beside a babbling creek. Lush greenery surrounds the area, creating a natural backdrop that enhances the peaceful atmosphere.
Home in Wevertown
4.97 out of 5 average rating, 154 reviews

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.

Guest favourite
A cozy seating area is highlighted by a brown leather sofa and a woven basket. A rug lies beneath, creating a comfortable ambiance. The adjoining wall displays the text 'ADK Stay' in a stylish font, adding a welcoming touch. Natural light enhances the space.
Flat in Schroon Lake
4.89 out of 5 average rating, 161 reviews

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!

Top guest favourite
A spacious living area features rustic wooden walls and high ceilings. A large, unique wood table is surrounded by bench seating. Soft seating options include a sofa and chair. A stone fireplace stands as a focal point, with large windows allowing natural light to enter.
Cabin in North Creek
4.91 out of 5 average rating, 409 reviews

Twilight Cabin

382 Back To Sodom Rd. WiFi, family-friendly activities and the beach. You’ll love my place because of the high ceilings, the location, the coziness, and the views. Built by a local craftsman with logs from our area and local river stone for the fireplace. Cabin is completely modernized. A lovely porch looking towards the pond and exterior lights along the Pond. Minutes to all outdoor activities. Pet fee $75 per pet must be paid at time of booking. Must bring dog blankets!

Top guest favourite
A bright living room features large windows framed with red-checkered curtains, allowing natural light to fill the space. A cozy couch and a coffee table are placed near a gas fireplace, while a wooden ceiling adds warmth to the design. A view of snow-covered outdoor surroundings is visible through the glass doors.
Cabin in Johnsburg
4.97 out of 5 average rating, 143 reviews

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)

Top guest favourite
A modern Scandinavian cabin is showcased, illuminated by soft lighting in the evening. A fire pit is centered in the snow-covered outdoor area, surrounded by wooden seating. The cabin features large glass doors that reveal a cozy interior, harmonizing with the natural surroundings.
Tiny home in North Hudson
4.92 out of 5 average rating, 112 reviews

Private ADK Tiny Home & Hot Tub for Two!

Stay Mountainbound is a Scandinavian- style cabin, tucked away in the Adirondacks. This refined retreat is designed with the modern couple in mind. This is the place for those wanting to get away from it all without sacrificing comfort and style. Privately located between pristine Schroon Lake and Keene Valley and within an hour drive to many high peaks and several world class ski resorts including Whiteface, Gore, and West Mountain.

Guest favourite
A rustic cabin with hand-split cedar shingles is surrounded by vibrant autumn foliage. Two white wooden chairs are positioned on the forest floor, offering a peaceful view of the cabin nestled among tall trees. The warm tones of the leaves enhance the natural setting.
Tiny home in North Creek
4.94 out of 5 average rating, 176 reviews

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.

Popular amenities for Chester holiday rentals

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