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Chestertown 4 Stars Hotels
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Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
8.8 out of 10, Excellent, (858)
The price is NT$7,248
NT$8,262 total
includes taxes & fees
Sep 2 - Sep 3

The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
9.4 out of 10, Exceptional, (414)
The price is NT$6,876
NT$8,410 total
includes taxes & fees
Sep 1 - Sep 2
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Sagamore Pendry Baltimore
1715 Thames St., Baltimore, MD
The price is NT$10,666 per night from Sep 9 to Sep 10
NT$10,666
NT$13,790 total
Sep 9 - Sep 10
includes taxes & fees
9.2/10 Wonderful! (1,002 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.

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Chestertown Hotels by Star Rating
Stay near popular Chestertown attractions
- Hotels near Washington College
- Hotels near Rolphs Wharf Marina
- Hotels near River Arts Chestertown
- Hotels near Historical Society of Kent County Maryland
- Hotels near Wilmer Park
- Hotels near Garfield Center for the Arts at the Prince Theater
- Hotels near Crumpton Auction
- Hotels near Baltimore Cruise Terminal
- Hotels near U.S. Naval Academy
- Hotels near Ripken Stadium
- Hotels near Chesapeake Bay Bridge
- Hotels near Sandy Point State Park
- Hotels near Annapolis City Dock
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Susquehanna River
- Hotels near White Marsh Mall
- Hotels near Fort McHenry
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Explore more hotels
- Hampton Inn & Suites Edgewood/Aberdeen-South
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