Holiday houses in Chester

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Top-rated holiday rentals in Chester

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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, 154 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 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, 259 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
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, 264 reviews

Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+

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, primary bedroom, loft w/ 2 sofa beds, desk, big lawn, grill, ski chair + LVL 2 EV charger. Fast Wi-Fi • Self check-in • Please read house rules!

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, 153 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, 167 reviews

Private Spacious Suite near Lakes, 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
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, 114 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.

Guest favourite
A rustic cabin with wooden siding is surrounded by lush greenery and trees. The building features a steep metal roof and multiple windows. A stone well is positioned in the foreground, enhancing the natural ambiance of the property.
Cabin in Wevertown
4.9 out of 5 average rating, 100 reviews

Riverview Cabin- Minutes to Gore Mt!

Welcome to The Hudson Hideaway, the perfect all season Adirondack Getaway. Relax and unwind at this unique and cozy cabin with a view of the Hudson River. Bring your fishing poles and tubes to fully enjoy the river in your own backyard! 0nly 10 minutes to Gore Mountain/North Creek and 25 minutes to Lake George. We are centrally located to a vast array of year round Adirondack adventures, including Rev Rail, hiking , skiing, snowshoeing, kayaking, and whitewater rafting.

Top Guest favourite
A charming bedroom features a spacious wooden bed, complemented by rustic decor. A bright kitchen area includes natural wood cabinetry and large windows showcasing the surrounding greenery. Outside, red Adirondack chairs are positioned near a fire pit, creating a cozy atmosphere for relaxation.
Cabin in Warrensburg
4.99 out of 5 average rating, 336 reviews

Romantic Lake George Getaway~Paula’s Silver Lining

*Escape the city life *Let the ways of nature put your mind, body and soul at ease *15 minutes to Lake George in the Adirondack Park *Vintage Record Player, Farm Fresh Eggs *Let the songbirds awaken you feeling like you are still dreaming *This is not just any five star stay step outside we have millions *We strive for our guests to have nothing less than a five star experience, as you can see by our reviews *Fire pit, hammock and grill available May-October

Top Guest favourite
A spacious kitchen features warm wood paneling and granite countertops. A large island with natural stone accents is surrounded by wooden stools. Stainless steel appliances, including a refrigerator and oven, are visible, along with ample cabinetry and windows providing natural light.
Cabin in North Creek
4.98 out of 5 average rating, 192 reviews

Gore Mountain Log Cabin Getaway

8 minutes to Gore Mountain. Perfect getaway for couples, family vacay, small sporting group, or long time friends. Log cabin located 5 mins to food & shopping. Summer offers gondola rides & short drive to lakes, fishing, boating; beautiful porch for morning coffee & lovely views. Gore Mountain in winter for skiing & snowboarding. 24 hour buffer between bookings from when guests check out. 3 night minimum stay on holidays. A/C unit in main room.

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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  4. Warren County
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