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 refundable
The price is NT$3,692 per night from Apr 26 to Apr 27
NT$3,692
NT$4,098 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (895 reviews)
The breakfast was as one would expect. Nothing unusual. I wish these hotels wouldn’t use so much plastic. Everything was clean. Chestertown is wonderful. Good restaurants. Much to see. The hotel is not fancy. Just a reliable place to be. Nothing unexpected. All good.
Reviewed on 2026/4/3
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is NT$4,132 per night from Apr 19 to Apr 20
NT$4,132
NT$5,803 total
Apr 19 - Apr 20
includes taxes & fees
9/10 Wonderful! (1,868 reviews)
Great historic building… felt like home away from home.
Reviewed on 2026/4/4
Hampton Inn Baltimore/Glen Burnie
6617 Ritchie Hwy Glen Burnie MD
Fully refundableReserve now, pay when you stay
The price is NT$3,338 per night from Apr 23 to Apr 24
NT$3,338
NT$3,806 total
Apr 23 - Apr 24
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
The shower had no cold water for two days it was boiling hot water that can damage my skin.I asked for house cleaning and when I came back nothing was done it was the same as I left.the next day I asked to make sure there was housecleaning coming to my room and they said yes I will make sure.That ...
Reviewed on 2026/4/5
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
Garfield Center for the Arts at the Prince Theater
You can get tickets for a performance at Garfield Center for the Arts at the Prince Theater on your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
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.
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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.
