Compare Villas, Resorts, & Rentals in Chestertown, New York, USA
About Chestertown Vacation Rentals
There are more than 165 incredible getaway rentals that are available in Chestertown. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Chestertown.
BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Chestertown, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Chestertown. Places to stay near Chestertown are 1184.07 ft² on average, with prices averaging GB £276 a night.
BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Chestertown. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods Chestertown, NY
Frequently Asked Questions About Chestertown?
What are the top hotels or resorts 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 hotels, resorts, or rentals are available in Chestertown?
BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2025 is over 165 in the Chestertown area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Chestertown.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Chester Shores Rental Villas and Private Getaways in Lake George, New York | 127 |
| Friends Lake Inn Rental Villas and Private Getaways in Lake George, New York | 129 |
