Holiday houses in Chestertown

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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 reviews

Romantic 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 reviews

Loon 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 reviews

House 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 reviews

The 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 reviews

Fully 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 reviews

Forest 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 reviews

Stay 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 reviews

Adirondack 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

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Warren County
  5. Chestertown