
Vacation rentals in Chester
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Top-rated vacation rentals in Chester
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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

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!

Butternut Adirondack Cabin.
Private stylish cabin. Expanded and newly Renovated. AC WiFi. Fireplace. Heating System. Full Kitchen, and bathroom with shower. Roku. In ground Pool shared by 5 other cabins. All new Furniture and new Queen Bed. Mill Creek neighbors the property for Trout fishing. Minutes to great skiing at Gore Mt. Minutes to Lake George and minutes to other Lakes, and Whitewater rafting and hiking. Guests to bring their own soaps and towels. $75 Per Pet Fee must bring pet covers for couches & bed.

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!!

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.

Adirondack Base Camp by Loon Lake and Gore Mt.!
Make great memories at this unique, rustic and family-friendly Adk base camp. This 1900 built, renovated barn is on 2.4 acres in walking distance to Loon Lake, 2 minute drive to the public beach and boat launch and a mere 20 minutes to Gore Ski Mountain! With trail heads right up the street, you can hike, bike, fish, hunt, ski, snowmobile, snowshoe, raft, kayak and tube, explore the region, R&R or sled on Dynamite Hill! 5 minutes off route 87, and 20 minutes from Lake George.

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)

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

Waterfront 1-bedroom apartment on 5 acres
This space has its own entrance/key and is attached but separate from the main house. Apartment has outstanding Western waterfront views and sunsets. Space is appropriate for 1-3 people and there is parking for 1 car. Guests have their own private apartment but shared outside amenities including patio, firepit, playset, yard, grill, kayaks, paddleboards, canoe, and dock seasonally May-September. Shared outdoor 7-person hot tub.
Popular amenities for Chester vacation rentals
Other great vacation rentals in Chester

Frostpine Cabin Near Gore Mountain

ADK cottage 5 minutes from Gore!

The Dowager Town Home

Riverfront Winter Escape | Near Gore & Lake George

Posh Camp a Classic Adk Mtn. Cabin & Guide Srvc.

Lily Pad North at Loon Lake near Gore Mountain

Fully Restored Barn ! The Alexander Ski Barn

Green Mansions Vacation Condo, 2 bedroom & 2 bath
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Mississauga Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- Lake George
- Saratoga Race Course
- Six Flags Great Escape Lodge & Indoor Water park
- The Wild Center
- West Mountain Ski Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Lake Flower
- Saratoga Spa State Park
- National Museum of Racing and Hall of Fame
- Adirondack Extreme Adventure Course
- Adirondak Loj
- Congress Park
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- Middlebury College
- Adirondack Animal Land
- Trout Lake




