Chestertown Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundable
The price is 3.270.698 ₫ per night from 3 May to 4 May
3.270.698 ₫
3.630.475 ₫ total
3 May - 4 May
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 3.404.333 ₫ per night from 19 Apr to 20 Apr
3.404.333 ₫
4.781.493 ₫ total
19 Apr - 20 Apr
includes taxes & fees
9/10 Wonderful! (1,871 reviews)
Yes
Reviewed on 9 Apr 2026
Hampton Inn Baltimore/Glen Burnie
6617 Ritchie Hwy Glen Burnie MD
Fully refundableReserve now, pay when you stay
The price is 2.676.828 ₫ per night from 10 May to 11 May
2.676.828 ₫
3.051.583 ₫ total
10 May - 11 May
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.
Popular places to visit
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
Garfield Center for the Arts at the Prince Theater
You can make plans for a show 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.
