
Chestertown Holidays
Photo by Patricia Knorr
- Plan, book, travel with confidence
Better together
Save up to €185 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top hotels in Chestertown

Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is €104 per night from 7 Sept to 8 Sept
€104
7 Sept - 8 Sept
includes taxes & fees
8.4/10 Very Good! (797 reviews)
"FEELS LIKE PEACEFULLY 👍 👌"
Reviewed on 14 Aug 2025

Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is €68 per night from 28 Aug to 29 Aug
€68
28 Aug - 29 Aug
includes taxes & fees
7.2/10 Good! (386 reviews)
"Great service"
Reviewed on 1 Aug 2025

The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
The price is €126 per night from 4 Sept to 5 Sept
€126
4 Sept - 5 Sept
includes taxes & fees
8/10 Very Good! (63 reviews)
"Perfect place to unwind. Great views of the harbor and marina. You get access to a private beach and there is a cute area for kids to play. The private beach provides chairs and umbrellas. The lodge also has a bar/food on site."
Reviewed on 16 Aug 2025
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
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.
Frequently asked questions
More trip options
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.