The best rentals from the top sites, all in one place

We believe finding a beachfront vacation rental in Chestertown should be easy and not take hours of searching and scrolling. We’ve designed VacationRenter from the ground up to help travelers find the perfect rental faster and easier.

Where to stay in Chestertown

Beachfront vacation rentals in Chestertown

There are 35 beachfront rentals near Chestertown for all manner or mood of traveling to the shoreline, availability of time off, and size of budget. So, if you are hoping for an affordable Chestertown Beach vacation, you can find 10% of the available rentals under $77/night. Or if you are willing to splurge on a luxury vacation in Chestertown, there are 4 between $399 and $987/night. Whether you are sleeping by yourself or with a significant other, or are travelling with a group of 16 there are short term home and apartment rentals in Chestertown near the beach to fit your Maryland vacation needs. The most popular types of beachfront rentals in Chestertown are houses, apartments and bed & breakfasts. Chestertown has been a frequently searched travel destination this year and continues to grow in popularity because of its beaches and other water activities. VacationRenter offers a wide selection of available beach vacation rentals from leading travel sites like VRBO (Vacation Rentals By Owner), Homeaway,, and many more. Search your travel dates to find available Chestertown vacation homes for your beach trip.

More Home-types in Chestertown

Chestertown has a variety of property types for you to consider when booking a trip. Here are the most popular property types in Chestertown:
- Oceanfront35 vacation rentals
- Beach35 vacation rentals
- House19 vacation rentals