Vacation rentals in Chestertown

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Popular amenities for Chestertown vacation rentals

Other great vacation rentals in Chestertown

Guest favorite
Cabin in Schroon Lake
4.98 out of 5 average rating, 90 reviews

The Treehouse

JillianRating, 5 stars8 months ago
Our stay at The Treehouse was wonderful. My family was immediately comfortable and loved our stay! Comfy beds, plenty of towels and lots of hooks and towel bars. The outdoor space was beautifully relaxing.
Top guest favorite
Home in Warrensburg
4.97 out of 5 average rating, 93 reviews

Lake George | Hot Tub | Firepit | Schroon Lake

Cornelia (Connie)Rating, 5 stars1 week ago
What a wonderful cabin in a peaceful area. Gary’s cabin is perfect. A nice place to relax after hiking and exploring the area. It was very cozy and had everything we needed. Gary responded quickly to any questions we had. We hope to return someday. Thank you Gary for making your cabin a wonderful place that feels like home.
Top guest favorite
Home in Warrensburg
4.97 out of 5 average rating, 29 reviews

River House

TylerRating, 5 stars5 days ago
There was no way I could pass up a chance to stay here. Beautiful surroundings, great location, easy to get to and private! Booked for an extended weekend fishing/golfing trip and had an amazing stay! Will definitely keep this place in mind when booking our next trip!
Top guest favorite
Home in Chestertown
5 out of 5 average rating, 33 reviews

The Hayes Homestead

JohnRating, 5 stars5 days ago
This is a great little spot, well-appointed for a family stay and was perfect for our travel needs with our small dog. Pet-friendly, safe, quiet, and lots of helpful extras around the house to make you feel right at home. We really enjoyed our stay here, and are only sad it wasn't longer! Would absolutely come back. Thank you!!
Guest favorite
Chalet in Chestertown
4.9 out of 5 average rating, 50 reviews

Loon Lake Luxury with kayaks and canoe

AndreaRating, 5 stars10 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!
Top guest favorite
Chalet in Chestertown
4.98 out of 5 average rating, 60 reviews

The Roost, a lake front 4 season home

Anna VictoriaRating, 5 stars2 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!
Top guest favorite
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 favorite
Cabin in Chestertown
4.87 out of 5 average rating, 23 reviews

Adirondack Escape - hiking, lake, golfing

CrystalRating, 5 stars2 weeks ago
A very peaceful stay in a beautiful, somewhat secluded location. Haley’s place is just as described. Would recommend!

Quick stats about vacation rentals in Chestertown

  • Total rentals

    10 properties

  • Nightly prices starting at

    G$18,823 GYD before taxes and fees

  • Total number of reviews

    290 reviews

  • Wifi availability

    10 properties include access to wifi

  • 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