Compare Cottages, Resorts, & Rentals in Chestertown, New York, USA
About Chestertown Vacation Rentals
There are over 200 amazing vacation rentals available in Chestertown. Choose from a variety of options including villas, hotels, and other rental properties. Explore a vast selection of luxury amenities at unbeatable prices, providing you with the ideal spot for your next getaway. Life is Better at the Cottage with Vacation Cottage, where you can discover fantastic stays in Chestertown.
Vacation Cottage offers numerous last-minute deals on villas, hotels, and rentals, both near you and across the globe. Whether you need accommodations for a group or event, such as a hotel or vacation rental (including cabins and private luxury villas), let us assist you. With Vacation Cottage in Chestertown, you can easily compare options from multiple suppliers with just a click to find the perfect price point, amenities, and style of stay for you. Whether you're seeking group discounts, private pools, hot tubs, pet-friendly options, or spacious master suite bedrooms with open-air showers, you can find it all with Vacation Cottage vacation rentals, resorts, and Airbnb-style properties in Chestertown. The average size of places to stay near Chestertown is approximately 1194.49 ftยฒ, with prices averaging $374 per night.
Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in Chestertown. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.
Find Vacation Cottage Rentals in these Cities and Neighborhoods Chestertown, NY
Frequently Asked Questions About Chestertown?
What are the top cottages, summer homes, and lake houses in Chestertown?
- Secluded and Cozy Townhome near Tripp Lake
- TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!
- 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
- Lakefront home steps away from a private, gentle sloping sandy beach & fire pit.
- Rustic Adirondack Retreat on Tripp Lake
- Same local favorite, an even better nightly rate, and now with NO CLEANING FEE!
- Modern Cabin w/Hot Tub-Minutes to Lakes & Skiing
How many rentals, hotels, or resorts are available in Chestertown?
Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 200 properties listed by Vacation Cottage in the Chestertown area for the year 2025, with this number increasing daily. By aggregating listings from various websites and travel providers, Vacation Cottage ensures a diverse array of choices for the best luxury stays in Chestertown.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Chester Shores Rental Cottages and Private Getaways in Lake George, New York | 127 |
| Friends Lake Inn Rental Cottages and Private Getaways in Lake George, New York | 129 |
