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Towns > Southern Region > Chestertown

Chestertown, NY

Chestertown, NY

Chestertown is a little community with a big presence. Here you can enjoy world-class restaurants, take a horseback ride along forested trails, ski miles of lighted cross-country trails, enjoy a free downhill ski and snowboard area with a rope tow, and an old-fashioned sledding hill. 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 Schroon River and the Hudson offer opportunities for whitewater rafting, kayaking, or fly fishing.

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Chestertown, NY Listings
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 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.
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.
Adirondack Contemporary Chestertown, NY
It will be a vacation to remember at Adirondack Contemporary in Chestertown, NY! This is an expansive, private rental home on the shores of Friends Lake with a private dock and Great Room that's perfect for family get-togethers.
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 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.
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.
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!
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!
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 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.
Showstopping Direct Friends Lake Retreat Chestertown, NY
Stay at Showstopping Direct, a five-bedroom rental house with antique furnishings and artwork combined with modern amenities, located on the shores of Friends Lake in Chestertown.
Summersong on Friends Lake Chestertown, NY
This delightful rental home in Chestertown 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 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 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!
Twin Pine Lodge Chestertown, NY
Our Authentic Log Homes and Rustic Adirondack Style Cottages offer great Adirondack Accommodations. Resting on 25 scenic acres of pristine Adirondack Mountains near Loon Lake, you'll find whatever you need!
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 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 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.
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 Carol Theater Chestertown, NY
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.