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 AED 372 per night from Mar 1 to Mar 2
AED 372
AED 412 total
1 Mar - 2 Mar
includes taxes & fees
8.4/10 Very Good! (872 reviews)
Polite and kind hotel manager
Reviewed on 25 January 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,884 reviews)
Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!
Reviewed on 31 January 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 AED 229 per night from Feb 22 to Feb 23
AED 229
AED 265 total
22 Feb - 23 Feb
includes taxes & fees
7/10 Good! (1,154 reviews)
Very nice stay, staff was very understanding and breakfast was amazing. Room was clean and we had no problems.
Reviewed on 4 February 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
Washington College
4/5(13 reviews)
Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
Wilmer Park
Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.
