
Chestertown Packages (Flight + Hotel)
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Top hotels in Chestertown

Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundable
The price is ฿3,691 per night from 26 Apr to 27 Apr
฿3,691
฿4,097 total
26 Apr - 27 Apr
includes taxes & fees
8.6/10 Excellent! (896 reviews)
N/A
Reviewed on 6 Apr 2026

Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is ฿4,142 per night from 19 Apr to 20 Apr
฿4,142
฿5,817 total
19 Apr - 20 Apr
includes taxes & fees
9/10 Wonderful! (1,873 reviews)
Valet parking is available. I received a bottle of wine as a gift, wow! The room is spacious but dark, there is no window to the outdoors. The window overlooks a closed-in courtyard that looks as it serves as events (weddings?) venue.
Reviewed on 11 Apr 2026

Hampton Inn Baltimore/Glen Burnie
6617 Ritchie Hwy Glen Burnie MD
Fully refundableReserve now, pay when you stay
The price is ฿3,126 per night from 26 Apr to 27 Apr
฿3,126
฿3,564 total
26 Apr - 27 Apr
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
The property had an issue with no cold water, and
Reviewed on 7 Apr 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
