Chestertown Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to Rp173.195 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundable
The price is Rp2.084.615 per night from 19 Apr to 20 Apr
Rp2.084.615
Rp2.313.923 total
19 Apr - 20 Apr
includes taxes & fees
8.6/10 Excellent! (893 reviews)
Clean, quiet.
Reviewed on 29 Mar 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is Rp2.198.103 per night from 19 Apr to 20 Apr
Rp2.198.103
Rp3.087.306 total
19 Apr - 20 Apr
includes taxes & fees
9/10 Wonderful! (1,870 reviews)
We had a great stay. Location couldn’t be better.
Reviewed on 31 Mar 2026
Hampton Inn Baltimore/Glen Burnie
6617 Ritchie Hwy Glen Burnie MD
Fully refundableReserve now, pay when you stay
The price is Rp1.589.347 per night from 12 Apr to 13 Apr
Rp1.589.347
Rp1.811.856 total
12 Apr - 13 Apr
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
A house problem means a one night local area stay. No issues with registration, good rate and clean room.
Reviewed on 30 Mar 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
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.
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
