Chestertown, NY

Large rooster statue outside of a restaurant in Chestertown NYChestertown is a little community with a big presence. Here you can enjoy a variety of restaurants, take a horseback ride along forested trails, ski miles of cross-country trails, and enjoy a free downhill ski and snowboard area with a rope tow. There's a 9-hole golf course located within Chestertown as well as an 18-hole course in nearby Warrensburg.

When it's time to relax, stroll the main street in search of that special gift or antique treasure. Indulge yourself at an old-fashioned ice cream parlor. Relax and enjoy a simple, uncomplicated lifestyle amid the beautiful scenery of the Adirondacks.

Visiting in the summer? Enjoy the many water activities in the area. Loon Lake near Chestertown offers boating, waterskiing and swimming. Try your hand at bullhead fishing, or enjoy the shimmering sunset on a dock with a good book. The nearby Schroon & Hudson Rivers offer opportunities for whitewater rafting, kayaking, or fly fishing.

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Chestertown, NY Listings
Our guest room &quote;Forest
Fern Lodge
Chestertown, NY
In the midst of the majestic Adirondack overlooking pristine Friends Lake, there stands a wondrous Guesthouse where luxurious lodging, sumptuous beds, indulgent baths & unforgettable breakfasts join an atmosphere of rustic elegance & lakeside living.
Friends Lake Inn
Friends Lake Inn
Chestertown, NY
A historic resort offering exclusive access to Friends Lake and an award winning restaurant and taproom. Enjoy fireplaces, private balconies, outdoor pool, and miles of hiking trails. Rates from $179 per night.
Exterior with room for 5 cars
Historic Adirondack Vacation House Rental - Sleeps Up to 20
Chestertown, NY
Our Adirondack Vacation House is located in the quaint Mountain village of Chestertown with convenience to shopping and dining in our fine restaurants. The house is very spacious which makes it ideal for an extended family, clean & nicely furnished.
Vacation at this beautiful lakefront property and have plenty of room to spread out with your family.
Adirondack Contemporary
Chestertown, NY
It will be a vacation to remember at this Adirondack Contemporary on the shores of Friends Lake in Chestertown, NY. This is an expansive, private rental home with a private dock and a Great Room that's perfect for family get-togethers.
There's room for the whole extended family to stay at Adirondack Dreaming!
Adirondack Dreaming
Chestertown, NY
This beautiful rental home right on the eastern shoreline of Friends Lake has an oversized great room, six bedrooms, three full baths, a campfire area, watercrafts, and more. You and your family won't want to leave!
All-American Properties in Chestertown, NY specializes in Adirondack Vacation Rentals!
All-American Properties
Chestertown, NY
Recognized as the greater Glens Falls Region's largest locally-owned real estate company, All-American Properties features a wide range of Adirondack vacation homes and area house rentals.
Take a group ride with friends or family members.
Circle B Ranch
Chestertown, NY
Located 15 minutes from Lake George, NY, Circle B is a family-owned and operated ranch offering group and private rides in which you can enjoy stunning Adirondack mountain views with your experienced guide.
Gallo Realty ~ Locally Owned & Operated ~ We Know the Area!
Gallo Realty ~ Locally Owned & Operated ~ We Know the Area!
Chestertown, NY
Specializing in Lakefront and Vacation Home Sales and Rentals on Brant, Schroon, Loon and Friends Lake. Open 7 days a week for the professional service you deserve! Located 1/4 mile off Exit 25 of I-87... just 20 minutes north of Lake George!
Stay at this camp and escape from your day-to-day routine.
Lakes End
Chestertown, NY
Stay at Lakes End, a five-bedroom rental house with antique furnishings and artwork combined with modern amenities, located on the shores of Friends Lake in Chestertown.
Loon Lake Serendipity is a medium-sized rental house located right on Loon Lake.
Loon Lake Serendipity
Chestertown, NY
Located on the southeastern end of Loon Lake in Chestertown, NY is a fantastic four bedroom rental house called Loon Lake Serendipity. With a main deck overlooking Loon Lake and tons of amenities, this house is perfect for an Adirondack getaway.
Najer Realty
Najer Realty
Chestertown, NY
Personalized guidance in your search for the Adirondack dream--whether it be a ski home in the mountains, lakefront retreat, year-round home or land to build a home. Visit our website for up-to-date listings and ways to contact us for an appointment.
Summersong on Friends Lake is in an ideal location to get away from it all with the family.
Summersong on Friends Lake
Chestertown, NY
This delightful vacation rental on Friends Lake includes a great room perfect for conversations while preparing meals, and a master bedroom with a private balcony. All the amenities you need for an ideal vacation will be right at your fingertips.
Sunset Point has a beautiful outdoor deck overlooking Loon Lake.
Sunset Point on Loon Lake
Chestertown, NY
Located directly on beautiful Loon Lake in Chestertown, NY, Sunset Point is a small and private rental house nestled in the woods. Featuring three bedrooms, a sandy beach, and more, Sunset Point has all you need for a true Adirondack vacation.
The Stone Lodge - Adirondack Vacation Rental on Loon Lake
The Stone Lodge - Adirondack Vacation Rental on Loon Lake
Chestertown, NY
The Stone Lodge is nestled in the middle of Blythewood Island on Loon Lake in Chestertown NY. With its own beach, it's a beautiful location with opportunities to swim, fish, golf, raft, canoe, ski, snowmobile, and so much more!
At Twin Pine Lodge, you can stay in a rustic cottage or authentic log cabin.
Twin Pine Lodge
Chestertown, NY
Located on 25 scenic acres of private land in the Adirondacks, Twin Pine Lodge is the premier choice for comfortable and affordable accommodations year round. The property features both authentic log homes and cozy, rustic cottages.
C+C Adirondack Snowmobile Tours
C+C Adirondack Snowmobile Tours
Chestertown, NY
Our staff of C+C Adirondack Snowmobile Tours has a combined 40+ years riding on the trails, so get ready for an exiting trip. We offer a range of riding that is suited for everyone from the beginner to the most advanced rider.
The Garden Spirit Labyrinth Design & Installation
The Garden Spirit Labyrinth Design & Installation
Chestertown, NY
Marjolaine creates different types of gardens at both private residences and public places, including labyrinths and sacred places, teaching others how to be a partner with nature through workshops, lectures, and retreats.
The Lakeside at Loon Lake
The Lakeside at Loon Lake
Chestertown, NY
Relax in the serene Adirondack Mountains and be close enough to all the activities. The Lakeside at Loon Lake lodging is only 15 minutes from Lake George Village and 15 minutes from the Gore Mountain Ski Area and Mountain Biking Center.
Chestertown Farmers' Market
Chestertown, NY
Spring, late summer, and early fall are perfect seasons for visiting farmers' markets. From the small, mom-and-pop stand at the corner, to the large, organized market with multiple vendors and extensive selections, it is definitely worth the trip.
Crossroads Outdoors Country Store and Sport Shop
Chestertown, NY
Gear up for your Adirondack adventure at the Crossroads Outdoors Country Store and Sport Shop in Chestertown, NY. The local store features a variety of great products as well as a deli and ice cream.
Dynamite Hill Recreation Center & Nature Trail
Chestertown, NY
Head on over to the Dynamite Hill Recreation Area for all sorts of fun activities, including cross-country ski trails, bicycling, hiking, snowshoeing, ice skating, and more!
Green Mansions Golf Club
Chestertown, NY
Located in the Southern Adirondacks, Green Mansions Golf Club features nine challenging holes, plus a driving range and pro shop. Looking for added excitement? Try one of their night time golf outings by flashlight!
Main Street Ice Cream Parlor & Restaurant
Chestertown, NY
For tasty icy treats, great food, and more, visit the Main Street Ice Cream Parlor & Restaurant in Chestertown, NY. The ice cream shop features an old-fashioned setting that is comfortable and nostalgic.
North Warren Chamber of Commerce
Chestertown, NY
The chamber directs visitors to local businesses in the North Warren area including the towns of: Pottersville, Loon Lake, Friends Lake, Chestertown, Schroon Lake, and Brant Lake.
Panther Mountain Pub
Chestertown, NY
Located at the Panther Mountain Inn in Chestertown, NY, Panther Mountain Pub specializes in all your pub food favorites and pizza. They also offer live music entertainment and a wide selection of craft beers at the bar.
Posh Primitive
Chestertown, NY
At Posh Primitive, you'll find custom made tents, queen-size beds, fresh linens, and an ideal location in the southern Adirondacks. Farm-to-table meals are provided, and well-behaved dogs are welcome.
The Bullhouse
Chestertown, NY
Located in the heart of Chestertown, NY, The Bullhouse is serving up Latin American cuisine in a casual yet upscale setting. Their menus include tasty tapas and appetizers, seafood, steaks, and great craft beers from the region.
The Carol Theater
Chestertown, NY
Three Lakes Ride
Visit the beautiful lakes of the Southeastern Adirondacks along the 33.2-mile Three Lakes Ride. Beginning in Chestertown, NY, this bike route passes by Brant Lake, Schroon Lake, and Loon Lake. It also features a mix of flat and rolling terrain.
Conway's Lake Manor
Chestertown, NY
Year round resort with free internet, private beach area, BBQ, air conditioning, and more! Just a 5 minute drive from Interstate 87.
The Adirondack Ramblewood House Rental with Beach/Dock
Chestertown, NY
Beautiful 6 bedroom 3 bathroom house. Large party/reception hall available. Do it yourself party/reception and save money.
The Original Lincoln Logs
Chestertown, NY
The log home. What could be more authentically American? And no one makes log homes quite the way we do. Learn how our products and services make your dream a reality.
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