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Top Chestertown Romantic Getaways & Hotels

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

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

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This vacation home features barbecue grills.
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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.

Chestertown hotels essential information

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1,023 hotels
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Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Recent Chestertown hotel reviews by fellow wanderers

Historic Inns of Annapolis

Historic Inns of Annapolis

5 out of 5
Posted 23 hours ago
Travelocity Verified Review
"What a charming property! I loved the location. I used valet parking, which worked smoothly. I would definitely stay here again."
A verified traveler stayed at Historic Inns of Annapolis
Historic Inns of Annapolis

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