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Romantic Hotels in Chestertown, Maryland

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Check availability on Chestertown Romantic Hotels

Tonight
Jul 28 - Jul 29
Tomorrow
Jul 29 - Jul 30
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Top Chestertown Romantic Hotels

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Enjoyed the stay! Beautiful place!"
Patricia 1-night trip
Posted 9 hours ago
Historic Inns of Annapolis

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, Rolphs Wharf Marina, 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.
What's the best hotel for couples in Chestertown?
Red Roof Inn & Suites Chestertown is a favorite hotel for couples, and features free WiFi and free parking.
How many romantic hotels will we be able to find in Chestertown?
Expedia has 7 romantic Chestertown hotels for you both to enjoy.
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, Rolphs Wharf Marina, or Garfield Center for the Arts at the Prince Theater 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.