Chestertown Vacations
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Find the Best Chestertown Vacation Packages
Chestertown Hotel Deals
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundableReserve now, pay when you stay
The price is ₩144,570 per night from Feb 24 to Feb 25
₩144,570
₩160,473 total
Feb 24 - Feb 25
includes taxes & fees
8.4/10 Very Good! (873 reviews)
Polite and kind hotel manager
Reviewed on Jan 25, 2026
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
Fully refundableReserve now, pay when you stay
The price is ₩92,404 per night from Feb 22 to Feb 23
₩92,404
₩106,726 total
Feb 22 - Feb 23
includes taxes & fees
7/10 Good! (1,158 reviews)
It was quiet and very clean‼️
Reviewed on Feb 10, 2026
Pendry Baltimore
1715 Thames St. Baltimore MD
Fully refundableReserve now, pay when you stay
The price is ₩531,326 per night from Mar 15 to Mar 16
₩531,326
₩683,692 total
Mar 15 - Mar 16
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Staff and room were amazing
Reviewed on Feb 7, 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.
Discover the most popular places to visit in Chestertown
Crumpton Auction
Take the family on an outing to Crumpton Auction during your trip to Chestertown. Take in the festivals while you're in the area.
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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.
