Holiday houses in Chestertown

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Top-rated holiday rentals in Chestertown

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Guest favourite
A cozy bedroom is depicted, featuring a wooden bed with a neutral-colored quilt and decorative pillows. Two bedside lamps provide soft lighting, complemented by a framed nature-themed artwork on the wall above the headboard.
Apartment in Chestertown
4.83 out of 5 average rating, 128 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

Top Guest favourite
Guest suite in Pottersville
4.99 out of 5 average rating, 156 reviews

Private Spacious Suite near Gore, Peaks, WOL-BI

Come & be rejuvenated at our spacious & peaceful suite located at the south end of Schroon Lake in Pottersville, NY. 25 mins to Gore Mt & 30 mins 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 favourite
The great room features vaulted wood ceilings with exposed beams and large windows allowing natural light. A comfortable blue sectional sofa is situated near a stone fireplace, while a dining area with a wooden table is visible in the background. The kitchen is defined by light wood cabinetry.
Home in Chestertown
4.97 out of 5 average rating, 103 reviews

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!

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, 247 reviews

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

Top Guest favourite
A cozy cottage is set amidst a lush green landscape, featuring a brown façade with large front windows. Satellite dishes are visible on the roof, while a grassy lawn surrounds the structure. Tall trees provide natural shade in the background.
Cabin in Warrensburg
4.96 out of 5 average rating, 105 reviews

Bearpine Cottage

Beautiful 2 bedroom Cottage with living room, kitchen , 1 bath - Ideal for small family up to 6 . Perfect for 4 people. (2 queen beds and a pull out queen in living room ) -Large screen porch -Large grassy lawn -Plenty of free parking -Wi-Fi -TV -The river is across the street. -7 minutes to Main street of Warresburg - 12 minutes to Main Street Lake George -10 minutes to Gore ski Mountain -minutes from ADK hiking trails all over - 5 minutes to Cronins golf Course on the river -Fire pit

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, 250 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.

Top Guest favourite
A cozy guest house is visible, surrounded by snow-covered trees and a white landscape. Fresh snow blankets the ground and the home's roof, while a clear path leads to the entrance. The exterior features warm orange siding, providing a contrast to the winter scene.
Home in Adirondack
5 out of 5 average rating, 170 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.

Top Guest favourite
The modern chalet-style home is set among tall trees, featuring a spacious wrap-around deck with outdoor seating. The peaked roof adds a distinct character, while large windows allow natural light to flood the interior. The sandy ground surrounds the lower level, enhancing the natural setting.
Chalet in Chestertown
4.98 out of 5 average rating, 168 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 favourite
A cozy seating area is highlighted by a brown leather sofa and a woven basket. A rug lies beneath, creating a comfortable ambiance. The adjoining wall displays the text 'ADK Stay' in a stylish font, adding a welcoming touch. Natural light enhances the space.
Apartment in Schroon Lake
4.89 out of 5 average rating, 161 reviews

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!

Top Guest favourite
A bright living room features large windows framed with red-checkered curtains, allowing natural light to fill the space. A cozy couch and a coffee table are placed near a gas fireplace, while a wooden ceiling adds warmth to the design. A view of snow-covered outdoor surroundings is visible through the glass doors.
Cabin in Johnsburg
4.97 out of 5 average rating, 143 reviews

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)

Top Guest favourite
Cabin in Warrensburg
5 out of 5 average rating, 117 reviews

Romantic Getaway at Firefly Mountain

* Romantic getaway nestled in the Adirondack Mountains, just 15 minutes from Lake George * Vintage record player, Farm fresh eggs, pollinator gardens * A dreamy escape into nature where you will wake up feeling like you are still dreaming * This is not just any five star stay step outside we have millions, our night sky is breathtaking * We strive for our guests to have nothing less than a five star experience * Firefly is decorated for Christmas Nov- New years

Top Guest favourite
Guest suite in Queensbury
4.97 out of 5 average rating, 360 reviews

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 Chestertown holiday rentals

Quick stats about holiday rentals in Chestertown

  • Nightly prices starting at

    Chestertown holiday rentals start at $135 AUD per night before taxes and fees

  • Verified guest reviews

    Over 290 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Chestertown rentals

  • 4.9 Average rating

    Chestertown stays are highly rated by guests—averaging 4.9 out of 5!

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