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

Find Romantic Hotels in Chestertown, MD

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Check availability on Chestertown Romantic Hotels

Tonight
Sep 9 - Sep 10
Tomorrow
Sep 10 - Sep 11
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Top Chestertown Hotel Reviews

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Excelente estadía volveré"
María Lucía ramos 1-night trip
Posted 10 hours ago
Hampton Inn Baltimore/Glen Burnie
Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Very convenient, right in the heart of town and near all the places that make Annapolis famous. Plus, its own bar in the basement, open five nights a week!"
Robert 4-night trip
Posted 15 hours ago
Historic Inns of Annapolis
Garner Hotel Glen Burnie BWI Airport Area by IHG

Garner Hotel Glen Burnie BWI Airport Area by IHG

10/10 Excellent
"."
Virginia 1-night trip
Posted 20 hours ago
Garner Hotel Glen Burnie BWI Airport Area by IHG
Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Balcony was a great option! Water Taxi excursion added to the trip!"
mary 2-night trip
Posted 2 days ago
Pendry Baltimore

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 Chestertown Historic District, Northern Chesapeake Bay, or 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 Chestertown Historic District, Northern Chesapeake Bay, or 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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