
Holiday houses in Chestertown
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Top-rated holiday rentals in Chestertown
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Chestertown holiday rentals
Other great holiday rentals in Chestertown
Top Guest favourite

Cabin in Warrensburg
5 out of 5 average rating, 87 reviewsRomantic Lake George Getaway~Firefly Mountain
MatanRating, 5 stars1 week ago
Had such a memorable time there, Paula was very kind to show us the nearby restaurants and always responded back right away if we had any questions. The area is always quiet and the small road is almost always empty so it’s nice to have a light walk there. Plenty of shops and restaurants just mins away as well as hikes and even waterfalls. Would highly recommend this stay!
Guest favourite

Chalet in Chestertown
4.9 out of 5 average rating, 50 reviewsLoon Lake Luxury with kayaks and canoe
AndreaRating, 5 stars11 months ago
We enjoyed our stay so much at DyAnn’s place - such a peaceful lake house, perfect for a family. We have 3 young kids and there was more than enough space. We experienced some storms and lost power and internet - host was very attentive and helpful, as was the automatic switch generator. This was by far the most well-stocked rental we’ve ever had. Area is quiet, not much for shops/restaurants, but so centrally located to other areas that we didn’t mind at all. We stayed very busy! We had a fantastic vacation at Loon Lake!
Superhost

Home in Chestertown
4.91 out of 5 average rating, 35 reviewsHouse in the Adirondacks, 15 min from Gore!
MarkRating, 5 stars4 months ago
Jon was easy to work with and always helpful. Everything is as described. We skied Mt Gore and it's a nice 15-20 minute drive in beautiful countryside. I imagine the place is extra beautiful in the summer in front of the lake. We were there with lots of snow. Jon's plow guy was prompt and courteous and helpful. Overall it was a great stay.
Top Guest favourite

Chalet in Chestertown
4.98 out of 5 average rating, 60 reviewsThe Roost, a lake front 4 season home
Anna VictoriaRating, 5 stars3 weeks ago
Here’s a polished Airbnb review for your Lake George stay: ⸻ We had a wonderful 4-day, 3-night stay at this lake house with our family! The home was spacious and well-equipped with all the amenities we needed for a comfortable getaway. We especially loved the kayaking and canoeing activities right on the property—it was a highlight for everyone! The location was perfect—just a short drive to town and Lake George Village, making it easy to explore and enjoy local attractions. While some of the furniture felt a bit outdated, it didn’t take away from the overall experience. A great stay for a relaxing and fun family vacation! We are already planning for a second trip next year!
Superhost

Barn in North Creek
5 out of 5 average rating, 4 reviewsFully Restored Barn ! The Alexander Barn
RebeccaRating, 5 stars2 months ago
We truly enjoyed our stay! The house was beautiful and it was in an excellent location for skiing at Gore. The gorgeous fireplace was so cozy, the kitchen was well equipped, and the bathrooms were immaculate. The heated floors in the bathroom and the fire pit outside were such nice added bonuses! We also loved the charming ambiance of the old fashioned gondola in the yard. Chris and Christin were amazing hosts and so helpful and responsive. We hope to come back in the future.
Top Guest favourite

Guesthouse in Chestertown
5 out of 5 average rating, 12 reviewsForest Lake Haven close to Gore Mt and Lake George
NicoleRating, 5 stars3 months ago
Loved staying at Gabriella’s place. Conveniently located and easy to find. We were arriving late and Gabriella made sure that the walkway was free of ice and snow (there had been some snowfall earlier). Absolutely spotless!! Will def stay here again.
Guest favourite

Tiny home in North Hudson
4.93 out of 5 average rating, 84 reviewsStay Mountainbound
R,L,NRating, 5 stars2 weeks ago
The cabin was beautiful and peaceful . The area is so beautiful with the woods. Only 15 minutes away is a town with many good restaurants and a lake. There are many hiking trails. We went for a peaceful weekend to just be together and relax . It could not have been more perfect. The host left many special touches.
Guest favourite

Cabin in Chestertown
4.88 out of 5 average rating, 25 reviewsAdirondack Escape - hiking, lake, golfing
MatthewRating, 5 stars1 week ago
The house was beautiful and very peaceful. Haley was an amazing host who made check-in flawless. Everything was clean and as described in the listing and we all loved the fireplace area for a late night relaxation. Being with a whole group who enjoyed golfing, having the golf course across the street was very convenient. I wouldn’t hesitate to stay again and would recommend this house to anyone looking to stay just outside of Lake George in a peaceful and relaxing environment.
Quick stats about holiday rentals in Chestertown
Total rentals
10 properties
Nightly prices starting at
$139 AUD before taxes and fees
Total number of reviews
290 reviews
Wi-Fi availability
10 properties include access to Wi-Fi
Popular amenities
Gym, BBQ grill and Laptop-friendly workspace
Local attractions
Main Street Ice Cream Parlor, The Bullhouse and Tops Friendly Markets
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- Saratoga Race Course
- Six Flags Great Escape Lodge & Indoor Water park
- Gore Mountain
- Pico Mountain Ski Resort
- West Mountain Ski Resort
- Saratoga Spa State Park
- Dorset Field Club
- Fort Ticonderoga
- Lake George Expedition Park
- Autumn Mountain Winery
- Whiteface Mountain Ski Resort
- National Museum of Racing and Hall of Fame
- Willard Mountain
- Adirondack Extreme Adventure Course
- Northern Cross Vineyard
- Lincoln Peak Vineyard
- Gooney Golf