The Best Romantic Hotels in Chestertown, MD in 2026

An aerial view of a town with a river, buildings, and surrounding greenery.

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Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

10/10 Excellent

"The room was clean and spacious, the breakfast had a good variety and was hot."

Pendry Baltimore

10/10 Excellent

"Beautiful hotel. Very clean and nicely decorated. Staff very friendly"

Country Inn & Suites by Radisson, Baltimore North, MD

8/10 Good

"The place was very quiet and not a lot going on. So if you like a more relaxed hotel, this is the place for you"

Frequently asked questions

Searching for romantic hotels in Chestertown?

Are you looking for a romantic vacation? You might consider checking out some of the nearby sights and attractions such as Historical Society of Kent County Maryland, Chestertown Historic District, or Northern Chesapeake Bay. 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.

When is the best time of year for a romantic getaway to Chestertown?

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.

What is there to do in Chestertown?

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 Historical Society of Kent County Maryland, Chestertown Historic District, or Northern Chesapeake Bay might be just the ticket when you're checking out the sights.

What's the best way to get to Chestertown and around town during my romantic getaway?

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.

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