Vacation Rentals in Chestertown, MD

Explore 20 vacation rentals near Chestertown, Maryland. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Chestertown, you can see photos of Chestertown vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Chestertown vacation rentals in specific areas. Whether you’re looking for a Chestertown staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Chestertown is $95 per night and the highest price is $2,263 per night.

2 of the vacation rentals near Chestertown are apartments or condos. The average bathroom count for this property type is 1. The median price for these vacation units is $113 per night. There are currently 1 vacation units under this price. 17 of the vacation rentals near Chestertown are houses. The average bathroom count for a vacation house near Chestertown is 4. The average price for vacation houses near Chestertown is $574 per night. There are 10 vacation homes under this price. The most common amenities for vacation rentals near Chestertown are: furnished, in-unit laundry, and air conditioning. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.