Compare Vacation Rentals & Rent By Owner Homes in Chestertown, New York, USA
About Chestertown Vacation Rentals
With more than 165 Chestertown vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Chestertown.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Chestertown, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Chestertown. Places to stay near Chestertown are 1184.07 ft² on average, with prices averaging US $371 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Chestertown with prices often at a 30-40% discount versus the price of a hotel. Just 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 vacation 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 Rentbyowner vacation rentals are available in Chestertown?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 165 in the Chestertown area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO 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 |
