Compare Villas, Resorts, & Rentals in Chestertown, New York, USA
About Casai's Private Villas and Holiday Rentals in Chestertown
Discover more than 165 vacation rentals available in Chestertown. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chestertown.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chestertown, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chestertown. On average, places to stay near Chestertown offer 1184.07 ft², with nightly prices averaging US $371.
With Casai, finding and comparing holiday rentals in Chestertown is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Chestertown, NY
Frequently Asked Questions About Chestertown?
What are the top holiday rentals in Chestertown?
- Eagles Nest at Loon Lake near Gore Mountain
- TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!
- Secluded and Cozy Townhome near Tripp Lake
- Loon Lake, Chestertown - Spotless, bright chalet, sleeps 6-8, near public beach
- Welcome home!
- The Roost, a lakefront 4 season home in the Adirondack Mountains
- Relax at Our River Retreat
- Rustic Adirondack Retreat on Tripp Lake
- Lakefront home steps away from a private, gentle sloping sandy beach & fire pit.
- Modern Cabin w/Hot Tub-Minutes to Lakes & Skiing
How many Casai.com holiday rentals are available in Chestertown?
As of 2025, Casai boasts over 165 properties listed in the Chestertown area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chestertown.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Chester Shores Vacation Rentals in Lake George, New York | 127 |
| Friends Lake Inn Vacation Rentals in Lake George, New York | 129 |
