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, 138 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
A cabin with large windows is framed by a wooden deck, surrounded by trees. Two red chairs are positioned near a stone fire pit, with logs arranged for a fire. A grassy area provides a natural setting, inviting outdoor relaxation.
Cabin in Johnsburg
4.97 out of 5 average rating, 153 reviews

2 bdrm ADK cabin 10 mins to GORE MTN

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

Top guest favourite
A charming cabin is nestled among tall pine trees beside a gently flowing stream. Lush green foliage surrounds the property, creating a natural, tranquil setting. The sound of water can be heard, enhancing the serene atmosphere of this rustic retreat.
Chalet in Johnsburg
4.95 out of 5 average rating, 248 reviews

Camp Shady - in the Adirondacks

Camp Shady is nestled on a few acres of pristine land with a stocked Trout Stream running thru the property. There is a great big fire pit with wood to burn, horseshoe pits and massive pines around the property. It has been all remodeled and is ten minutes from Gore Mountain. There is a television with lots of DVD's, access to the internet & cell phone reception on the premises. There is a landline, board games, and an JBL speaker to play your music thru. Get unplugged, paradise awaits!

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, 257 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.

Guest favourite
A hot tub is situated on a wooden deck overlooking a winter landscape. Snow-covered trees surround the area, with a serene ambiance created by the falling snowflakes. Steam rises gently from the water, inviting relaxation amid the tranquil scene.
Home in Chestertown
4.92 out of 5 average rating, 120 reviews

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.

Top guest favourite
Home in Adirondack
5 out of 5 average rating, 177 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
The modern chalet-style home is set among tall trees, featuring a spacious wrap-around deck with outdoor seating. The peaked roof adds a distinct character, while large windows allow natural light to flood the interior. The sandy ground surrounds the lower level, enhancing the natural setting.
Chalet in Chestertown
4.98 out of 5 average rating, 171 reviews

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.

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, 112 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, 162 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.

Top guest favourite
A spacious log cabin exterior is surrounded by greenery. The deck features a red umbrella and an American flag is displayed on the stone-walled front. A gravel driveway leads to the cabin, which includes a two-car garage and large windows allowing natural light inside.
Flat in Chestertown
5 out of 5 average rating, 119 reviews

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!

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.

Top guest favourite
The exterior of a classic A-frame cabin is shown, surrounded by tall trees. A spacious wooden balcony with a railing extends from the second floor, offering views of the forest. The steeply pitched roof complements the rustic architecture, creating a charming and inviting presence.
Cabin in Schroon Lake
4.98 out of 5 average rating, 109 reviews

The Treehouse

Experience the cozy and rustic charm of this classic A-frame cabin. Perched in a hemlock forest at the edge of the Pharaoh Lake Wilderness, the Treehouse is the perfect setting for an Adirondack getaway. Nature will greet you at the door while the comforts of home await inside. The Schroon Lake Village and various attractions, amenities and outdoor excursions are just a short drive away.

Popular amenities for Chester holiday rentals

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