Chestertown Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Patricia Knorr
Top hotels in Chestertown
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is 2.135.322 ₫ per night from 16 Oct to 17 Oct
2.135.322 ₫
2.370.208 ₫ total
16 Oct - 17 Oct
includes taxes & fees
7.2/10 Good! (400 reviews)
"Wish they had the pool open. The staff is great here and very helpful."
Reviewed on 6 Oct 2025
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is 2.688.924 ₫ per night from 19 Oct to 20 Oct
2.688.924 ₫
2.984.705 ₫ total
19 Oct - 20 Oct
includes taxes & fees
8.4/10 Very Good! (825 reviews)
"Nice hotel"
Reviewed on 29 Sept 2025
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
Fully refundable
The price is 3.487.693 ₫ per night from 12 Oct to 13 Oct
3.487.693 ₫
3.987.478 ₫ total
12 Oct - 13 Oct
includes taxes & fees
7.8/10 Good! (70 reviews)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"
Reviewed on 5 Sept 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
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
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.
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.
