
Find 4 Star Hotels in Chestertown, MD from AED 729
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Our top choices for Chestertown 4-star hotels

Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph CollectionHistoric District
8.8 out of 10, Excellent, (898 reviews)
The price is AED 684
AED 779 total
includes taxes & fees
1 Feb - 2 Feb

9.4 out of 10, Exceptional, (434 reviews)
The price is AED 573
AED 729 total
includes taxes & fees
1 Feb - 2 Feb
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Explore similar 5-star hotels
Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Chestertown.

Pendry Baltimore
1715 Thames St. Baltimore MD
The price is AED 1,219 per night from Feb 17 to Feb 18
AED 1,219
AED 1,584 total
17 Feb - 18 Feb
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
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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.
Learn more about Chestertown
Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbor.

Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection
10/10 Excellent
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Stay near popular Chestertown attractions
- Hotels near Washington College
- Hotels near Wilmer Park
- Hotels near River Arts Chestertown
- Hotels near Historical Society of Kent County Maryland
- Hotels near Rolphs Wharf Marina
- Hotels near Garfield Center for the Arts at the Prince Theater
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- Hotels near U.S. Naval Academy
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