Romantic Hotels in Chestertown, MD

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Apr 21 - Apr 22
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Featured Chestertown Romantic Getaways & Hotels

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

At this vacation home, guests have access to features like laundry facilities. This family-friendly vacation home also has barbecue grills.
Breakfast included
Kitchen
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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.

Can't wait to surprise your other half with an impromptu few days away? Or maybe you're eager to impress that someone special with a lavish hotel stay? Whatever type of romantic escape you have in mind, there's bound to be something that makes your heart flutter in Chestertown.

Chestertown hotels essential information

Accommodation
1,070 hotels
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Highest Price
Popular hotels
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Recent Romantic Getaways & Hotels Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

5/5 Excellent
Historic Inn Historic Views
"Frequent visitor, and booked a room with two double beds this time. The room was actually spacious (not all of their rooms are) and the beds and bedding were very comfortable. Nice view of Main Street Annapolis and the State House. Can't beat the location or the history. Note that you will NOT be able to check in even slightly early though."
A verified traveler stayed at Historic Inns of Annapolis
Posted 1 day ago
Historic Inns of Annapolis

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