Find 5 Star Hotels in Chestertown, MD from SAR 626
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Compare Chestertown 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Pendry Baltimore
Fells Point
9.4 out of 10, Exceptional, (1004)
The price is SAR 1,185
SAR 1,547 total
includes taxes & fees
25 Dec - 26 Dec
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Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Chestertown.

Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
The price is SAR 549 per night from Dec 18 to Dec 19
SAR 549
SAR 626 total
18 Dec - 19 Dec
includes taxes & fees
8.8/10 Excellent! (876 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

Pendry Baltimore
10/10 Excellent
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Stay near popular Chestertown attractions
- Hotels near Washington College
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