Find Romantic Hotels in Chestertown, MD

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Our top choices for Chestertown romantic hotels

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (151 reviews)
"Great house for a quick little getaway with family. The house is perfect for families with children; relaxed and friendly, not fussy. Would definitely recommend."
United States
Alison R.
The price is AED 889
AED 1,865 total
includes taxes & fees
5 May - 6 May
5-bedroom vacation home 5 minutes from historic Charlestown

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (76 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is AED 771
AED 1,558 total
includes taxes & fees
5 May - 6 May
Cozy 2br home w/ parking in downtown Annapolis

Beachcomber Suite

Beachcomber Suite
Kent County
The price is AED 536
AED 662 total
includes taxes & fees
4 May - 5 May
Beachcomber Suite

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
The price is AED 1,322
AED 2,424 total
includes taxes & fees
4 May - 5 May
Chesapeake Cottages- 2 Quaint Waterfront Retreats
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.

Top Chestertown Hotel Reviews

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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 Northern Chesapeake Bay, Chesapeake Bay, or Historical Society of Kent County Maryland. 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 Northern Chesapeake Bay, Chesapeake Bay, or Historical Society of Kent County Maryland 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.