Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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Guest favourite
A charming two-story home sits surrounded by greenery, featuring a red wooden exterior with white trim. The structure includes multiple windows, providing natural light. A gravel driveway leads to the entrance, with the yard showcasing a lush landscape and a few trees in the vicinity.
Home in North Creek
4.96 out of 5 average rating, 155 reviews

Beautiful Renovated Adirondack Getaway min to Gore

Stay in North Creek village, in the heart of the Adirondack Mountains, in this beautiful, fully refurbished 1840s home. This 4-bedroom, 2-bath house has been completely updated to offer the perfect balance of modern amenities and historic, exposed architecture. Perfect getaway for those who love to hike, mountain bike, whitewater raft, kayak, ski, or just explore the beautiful outdoors. Conveniently located minutes from town center, Gore Mountain, and various hiking trails. 30 min to Lake George

Guest favourite
Tiny home in North Creek
4.85 out of 5 average rating, 126 reviews

Cozy ski getaway for 2-minutes from Gore

Welcome to our charming Tiny House Retreat offering a unique escape from the hustle & bustle of daily life on 3.1 scenic acres. Situated just beyond the edge of town around a bend that makes it feel very private & surrounded by nature, it is a short walk/bike ride to the downtown area w/restaurants & shopping. Sip your morning coffee overlooking the Hudson River & at the end of your day, unwind under the starry Adirondack skies around the campfire after enjoying a beautiful view of the sunset.

Guest favourite
The great room features vaulted wood ceilings with exposed beams and large windows allowing natural light. A comfortable blue sectional sofa is situated near a stone fireplace, while a dining area with a wooden table is visible in the background. The kitchen is defined by light wood cabinetry.
Home in Chestertown
4.97 out of 5 average rating, 106 reviews

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!

Top guest favourite
The exterior of a red wooden house features large glass doors framed by light curtains. A spacious deck extends in front, equipped with a covered grill and picnic table. Triangular windows above the doors add architectural interest, surrounded by a wooded setting.
Home in Chestertown
4.95 out of 5 average rating, 253 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 vibrant garden surrounds a rustic barn, featuring a variety of flowers in differing colors, including reds, yellows, purples, and whites. Lush greenery complements the blossoms, while the barn's weathered wooden facade is visible in the background, contributing to the serene outdoor setting.
Loft in North Creek
5 out of 5 average rating, 141 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
Guest suite in Pottersville
4.99 out of 5 average rating, 160 reviews

Private Spacious Suite near Gore, Peaks & WOL-BI

Surround yourself with peace & tranquility in our spacious suite located at the south end of Schroon Lake. 25 mins to ski Gore& 30 mins to hike in 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!

Top guest favourite
Cabin in North Creek
4.98 out of 5 average rating, 109 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, 157 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 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, 147 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
Camper van/Motorhome in Johnsburg
4.97 out of 5 average rating, 110 reviews

Happy Camper!

Guests must walk 420ft from the parking spot through the woods to reach the RV. There is a cart / sled for you to use. *In WINTER* 4x4/AWL Drive Required 2W Drive Vehicles Proceed at your own risk Private, year-round, 4 person Hot tub! 420 Friendly! There may be beer in the fridge. Over the years guests have started a "Take a Beer Leave a Beer" tradition. Pets Welcome! CHECK IN 4PM - 8PM Wood for sale on site! $10 Large wood bundles

Guest favourite
The cabin is nestled among lush greenery, with a stream flowing nearby. Outdoor seating is arranged around a fire pit, complemented by logs for seating. The structure features a welcoming entrance with large windows, enhancing the natural light in the space.
Cabin in North Creek
4.93 out of 5 average rating, 115 reviews

The Cozy Cabin 1/4th of a Mile to Gore Mountain!

Stay at the Cozy Cabin for your next winter adventure! Only 1/4th of a mile to the entrance of Gore this is the perfect spot for your next ski trip. A short drive to all that North Creek has to offer including several great restaurants and shops. High speed internet / Roku TV. Enjoy hanging out by the wood stove on a chilly winter night. Book the Cozy Cabin today and plan your next winter vacation!

Guest favourite
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.

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