Vacation rentals in Chestertown

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Top-rated vacation rentals in Chestertown

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Guest favorite

Home in Wevertown

4.98 out of 5 average rating, 131 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 hiking, mountain biking, kayaking, rafting and fishing are all within 15 minutes of our location. SEASONAL DISCOUNTS AVAILABLE! Please inquire.

Guest favorite

Rental unit in Chestertown

4.82 out of 5 average rating, 116 reviews

Lily Pad North at Loon Lake near Gore Mountain

**COVID-19 Update ** We have implemented enhance cleaning procedures including the use of disinfectants on high touch surfaces. We recently replaced all linens with commercial linens to withstand hot water washing and drying at high temps. We also provide anti-viral and anti-bacterial cleaners in each property. We request that all visitors follow NYS and local Covid-19 guidelines. The Lily Pad North at Loon Lake in Chestertown, NY is nestled in the Adirondack Mountains of upstate New York and r

Guest favorite

Chalet in Warrensburg

4.99 out of 5 average rating, 102 reviews

ADK River Rapture- Warrensburg/Lk George/Gore Mntn

Elegant 3BR/3BaR Waterfront home with river access minutes from Lake George & Gore Mountain...river, lake & ski fun abound! Wraparound deck & floor to ceiling windows offer stunning Hudson River and mountain views from all angles. Open concept main floor has cathedral ceiling, magnificent stone fireplace in Great Room, custom hardwood floors, new granite kitchen & 3 spacious upstair BR's. Master BR offers a private, en suite bath while 2 guest bedrooms share another full bath. Total tranquility!

Guest favorite

Barn in Chestertown

4.96 out of 5 average rating, 185 reviews

Red Barn Guesthouse. Lawn & Patio. Hot Tub! LV2 EV

Relax in this cozy barn! With a little rustic flair the inside is loaded with luxurious amenities. 1min off I-87 1min Schroon River 2mins Loon Lake 5mins Brant Lake 25mins Gore Mountain 25mins Lake George Tons of nearby hikes! This is the perfect place to rest your head. Soak in the Hot Tub. There's a full kitchen, dining area, loft with 2 sofa beds, a private bedroom, desk, spa-like shower & a large lawn with a BBQ, ski chair swing, & fire pit. LVL 2 EV. PLEASE READ HOUSE RULES BEFORE BOOKING

Guest favorite

Guest suite in Pottersville

4.99 out of 5 average rating, 127 reviews

Private & Serene Suite Near Gore-Peaks-WOL/BI

Come & be rejuvenated at our spacious & inviting Loft Suite at the south end of Schroon Lake in Pottersville, NY. 25 mins to Gore Mt & 30 minutes to hiking 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!!

Guest favorite

Home in Minerva

4.96 out of 5 average rating, 101 reviews

Cozy Central Adirondack Charmer

Quaint two-bedroom, one bath home located in the Central Adirondacks close to everything. Comfortable with amenities including WIFI, Smart TV, and washer/dryer. Minutes off I-87. Less than 10 miles to Gore Mountain Ski Resort and Hudson River rafting. Easy High Peaks access for hiking, biking and paddling. Snowmobiling and cross-country skiing nearby. 3 miles to Minerva Lake. Schroon Lake and Lake George are easy drives. A carefree home base for all your four-season recreational needs.

Guest favorite

Home in Adirondack

5 out of 5 average rating, 152 reviews

Adirondack Owl's Nest Guest House

Our Adirondack Guest House is centrally located to many nearby attractions the region has to offer. Located on 10 wooded acres, just minutes off Northway I-87. Only 2 miles from Schroon Lake boat launch and Word of Life. Minutes to Brant Lake & Loon Lake. A short drive to beautiful Lake George and nearby Gore Mountain. The area offers: swimming, hiking, bicycling, fishing, golfing, canoeing & kayaking, river tubing, adventure course, rodeos, skiing, snowshoeing, sledding, & snowmobiling.

Guest favorite

Chalet in Chestertown

4.98 out of 5 average rating, 149 reviews

Chalet on Loon Lake (Gore Mt. 20 min.)

Located on beautiful Loon Lake, this modern chalet style home, with private beach and dock, features an open floor plan with 4 bedrooms, 2 full baths and loft. The house is fully furnished and has all the creature comforts. Outdoor amenities include a wrap-around deck and outdoor dining furniture. Enjoy boating, fishing, hiking, skiing and snowmobiling. Located just 30 minutes from Lake George and 20 minutes from Gore Mountain and the North Creek Ski Bowl and cross county trail system.

Guest favorite

Cottage in Adirondack

5 out of 5 average rating, 232 reviews

Water's Edge at Beaver Pond

Like being on a boathouse, this unique custom cottage/camp embraces the spirit of Adirondack lakehouse living... with a breathtaking view from every room! Perched on the shore of private Beaver Pond, this pristine lake offers great recreational activities (canoe/ kayak/ paddleboard/ swimming/ fishing). Inside the cottage, this home is designed with every detail carefully selected, and all modern amenities included! Cozy, comfortable and well-appointed... a perfect vacation location!

Guest favorite

Home in Chestertown

4.92 out of 5 average rating, 156 reviews

The Stone Lodge on Blythewood Island in Loon Lake

Looking for an all-season getaway in the Adirondacks? Come enjoy our lake and mountain views at the historic Stone Lodge on Blythewood Island in Loon Lake in Chestertown, NY. Our family has lived on the Island for more than 60 years. We welcome you to join us! The Stone Lodge was brought back to its original ambiance 7 years ago, when the Monroe family made it a place where others could enjoy the beauty, sights and sounds of nature from a beautiful authentic Adirondack retreat.

Guest favorite

Home in Warrensburg

4.91 out of 5 average rating, 136 reviews

Adirondack Bungalow getaway

Cozy stand-alone bungalow is perfect for a hiking getaway or an amazing week touring breweries and wineries in the Adirondacks. Features a beautiful decorative fenced yard, with seasonal patio and outdoor gas fire table. Enjoy evenings on the open air porch and walk out your back door to Hackensack Mountain's trailhead. Just minutes away from downtown Lake George attractions. Leave your hiking gear or winter ski equipment out of site in the mudroom/laundry room.

Guest favorite

Loft in Brant Lake

4.96 out of 5 average rating, 207 reviews

Cozy Adirondack Efficiency

Located 18 miles from Gore Mountain, 2 miles from Brant Lake and 1.5 miles from the Schroon River, this cozy Adirondack efficiency allows guests to experience all that the North Country has to offer with the comfort of modern amenities. Ample space for parking makes this efficiency ideal for those pulling snowmobiles, boats, and jet skis. The efficiency is located on the second story of an unoccupied building--guests will have the entire space to themselves.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chestertown vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Chestertown's top sights

Main Street Ice Cream Parlor50 locals recommend

The Bullhouse33 locals recommend

Tops Friendly Markets28 locals recommend

The Crossroads28 locals recommend

Odd Duck20 locals recommend

Dynamite Hill Recreation Area20 locals recommend

Other great vacation rentals in Chestertown

Guest favorite

Home in Brant Lake

5 out of 5 average rating, 29 reviews

The Refuge at Brant Lake!

Guest favorite

Home in Warrensburg

4.97 out of 5 average rating, 65 reviews

Lake George | Hot Tub | Firepit | Schroon Lake

Guest favorite

Home in Warrensburg

4.94 out of 5 average rating, 18 reviews

River House

Guest favorite

Home in Chestertown

5 out of 5 average rating, 32 reviews

Blue Bay Retreat - Loon Lake Lakefront w/ Hot Tub

Guest favorite

Home in Chestertown

5 out of 5 average rating, 28 reviews

The Hayes Homestead

Guest favorite

Home in Chestertown

4.93 out of 5 average rating, 75 reviews

North Pine Lodge @ Loon Lake, ADK adventure awaits

Guest favorite

Home in Adirondack

5 out of 5 average rating, 89 reviews

Winter Wonderland/ Summer Solitude

Guest favorite

Cabin in Brant Lake

4.98 out of 5 average rating, 57 reviews

Lake George Cabin-Fireplace-Firepit-Gameroom

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Quick stats about vacation rentals in Chestertown

Total rentals
10 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
270 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Main Street Ice Cream Parlor, Tops Friendly Markets, and The Bullhouse

Vacation rentals in Chestertown

Top-rated vacation rentals in Chestertown

Home in Wevertown

Rental unit in Chestertown

Chalet in Warrensburg

Barn in Chestertown

Guest suite in Pottersville

Home in Minerva

Home in Adirondack

Chalet in Chestertown

Cottage in Adirondack

Home in Chestertown

Home in Warrensburg

Loft in Brant Lake

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Chestertown vacation rentals

Stay near Chestertown's top sights

Other great vacation rentals in Chestertown

Home in Brant Lake

Home in Warrensburg

Home in Warrensburg

Home in Chestertown

Home in Chestertown

Home in Chestertown

Home in Adirondack

Cabin in Brant Lake

Quick stats about vacation rentals in Chestertown

Total rentals

Nightly prices starting at

Total number of reviews

Wifi availability

Popular amenities

Local attractions

Destinations to explore