Photo by Assya A
Plan, book, travel with confidence
Better together
Save up to NZ$545 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
Our pick of the best Chestertown Hotel Deals
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$154 per night from 29 May to 30 May
NZ$154
per night
29 May - 30 May
7.2/10 Good! (267 reviews)
"Sometimes, you don’t need a fancy place; just a clean place. That’s what this is. Maybe there weren’t the newest finishes, but we really appreciated having the extra pull-out couch and space in the room. It was perfect for traveling with my 3 teenagers."
Reviewed on 20 May 2024
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$226 per night from 29 May to 30 May
NZ$226
per night
29 May - 30 May
8.4/10 Very Good! (676 reviews)
"The onsite manager was very helpful. The staff was very nice."
Reviewed on 13 May 2024
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$298 per night from 16 Jun to 17 Jun
NZ$298
per night
16 Jun - 17 Jun
8.8/10 Excellent! (1,614 reviews)
"overall the room was very clean, very spacious and service with housekeeping was fabulous. The only complain we had was we kept hearing this noise coming from the wall like if there was some kind of machine that kept going off and on, humming sound"
Reviewed on 23 May 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
Discover the most popular places to visit in Chestertown
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 holiday ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.