![](https://mediaim.expedia.com/destination/2/6785bfdbe6f67238f03adb254741e2d9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Chestertown Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Assya A
Plan, book, travel with confidence
Better together
Save up to Rp10 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
![Red Roof Inn & Suites Chestertown](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/0d84b7e3_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is Rp1.329.372 per night from 24 Jun to 25 Jun
Rp1.329.372
per night
24 Jun - 25 Jun
7.2/10 Good! (280 reviews)
"Not exceptional, but clean."
Reviewed on 16 Jun 2024
![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/d4e0c3f2_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is Rp2.103.034 per night from 24 Jun to 25 Jun
Rp2.103.034
per night
24 Jun - 25 Jun
8.4/10 Very Good! (680 reviews)
"It was great"
Reviewed on 3 Jun 2024
![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/5c9aedf4_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is Rp2.247.377 per night from 2 Jul to 3 Jul
Rp2.247.377
per night
2 Jul - 3 Jul
8.8/10 Excellent! (1,631 reviews)
Weekend getaway.
"Easy check in. Friendly staff. Located only a short walk to the waterfront. Will definitely stay here again."
Reviewed on 17 Jun 2024
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.
Frequently asked questions
Popular places to visit
Washington College
Enjoy the student vibe when you visit 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.
River Arts Chestertown
Enjoy the student vibe when you visit River Arts Chestertown during your trip to Chestertown. Take in the festivals in this family-friendly area.
More trip options
Hotels
Hotels with smoking rooms in JamestownHotels with smoking rooms in SanfordHotels with smoking rooms in Mountain HomeHotels with smoking rooms in DanvilleHotels with smoking rooms in CookevilleGay-Friendly Hotels in Hot SpringsHotels with smoking rooms in CollinsvilleHotels in IthacaHotels with smoking rooms in PoughkeepsieHotels with smoking rooms in KingslandHotels with smoking rooms in Glen BurnieHotels with smoking rooms in RollaHotels with Entertainment in Ocean City
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.