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Find Romantic Hotels in Chestertown, MD

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Pick from 5 Chestertown Romantic Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
looking down river from the dock
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
9.8 out of 10, Exceptional, (79)
"House was even better than the photos showed. We spent evenings out on the dock watvhing the river and beautiful views. The hosts thought of every detail for a perfect stay."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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 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.
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 to visit 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 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.
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.