Romantic Hotels in Chestertown, Maryland

Are you looking for a romantic vacation? You might consider checking out some of the nearby sights and attractions such as Rolphs Wharf Marina, Historical Society of Kent County Maryland, or Garfield Center for the Arts at the Prince Theater. If you’re interested in staying close to a certain attraction, you can sort properties by neighborhood or distance to top landmarks, so you’ll be able to see everything on your list.

Red Roof Inn & Suites Chestertown is a favorite hotel for couples, and features free WiFi and free parking.

Expedia has 7 romantic Chestertown hotels for you both to enjoy.

If you’re looking forward to lots of outings with your partner, check out these details about year-round temperatures in Chestertown: The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.

There’s nothing better than seeing a new place with your sweetheart, so consider taking time to discover all that Chestertown has to offer. A visit to Rolphs Wharf Marina, Historical Society of Kent County Maryland, or Garfield Center for the Arts at the Prince Theater might be just the ticket when you’re checking out the sights.

These transportation options in Chestertown might help your romantic getaway go off without a hitch: To get to Chestertown, book a flight to Baltimore, MD (MTN-Martin State), which is the closest major airport, located 20.3 mi (32.7 km) from the city center. If you’d like to explore around the area, consider renting a car to take in more sights.