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

We believe finding a 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

Vacation rentals in Chestertown

There are 102 vacation rentals near Chestertown for all manner or mood of travel, availability of time off, and size of budget. So, if you are hoping for an affordable Chestertown vacation, you can find 10% rentals under $75/night. Or if you are willing to splurge on a luxury vacation in Chestertown, there are 10 between $597 and $2,177/night. Whether you are sleeping by yourself or with a significant other, or are travelling with a group of 37 there are short term home and apartment rentals in Chestertown to fit your Maryland vacation needs. The most popular types of short-term rental homes in Chestertown are houses, private rooms and bed & breakfasts. Chestertown has been a frequently searched travel destination this year and continues to grow in popularity. VacationRenter offers a wide selection of vacation rental availability 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 trip.

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:
- Oceanfront102 vacation rentals
- Beach102 vacation rentals
- House49 vacation rentals
- Private Room14 vacation rentals
- Bed & Breakfast12 vacation rentals

Points of interests in Chestertown

Chestertown has several popular points of interest for you to check out when visiting the area. Here are the most popular points of interest in Chestertown:
- Historical Society-Kent County: 790 vacation rentals
- MassoniArt Gallery: 790 vacation rentals
- John L Stam House: 790 vacation rentals
- Sultana Education Foundation: 790 vacation rentals
- Wilmer Park: 790 vacation rentals
- Widehall: 790 vacation rentals