Chestertown adirondack Vacation Rentals by Owner.Before booking, read recent guest reviews to ensure the property meets your expectations.Several properties welcome pets, allowing you to bring your furry companions along.Many rentals are situated near lakes, providing serene water views and access to activities like swimming and kayaking.Chestertown, New York, nestled in the Adirondack Mountains, offers a variety of vacation rentals by owners, including houses, cabins, and cottages. Chestertown adirondack Vacation Rentals by Owner.