Chestertown Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundable
The price is 2.793.388 ₫ per night from 21 Jun to 22 Jun
2.793.388 ₫
3.100.662 ₫ total
21 Jun - 22 Jun
includes taxes & fees
8.6/10 Excellent! (915 reviews)
"my favorite place to stay when going to Chestertown. Recommend this hotel vs any other in the area"
Reviewed on 28 May 2026
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is 1.894.299 ₫ per night from 8 Jun to 9 Jun
1.894.299 ₫
2.102.671 ₫ total
8 Jun - 9 Jun
includes taxes & fees
7.2/10 Good! (449 reviews)
"The staff at the front is very rude. Everytime I would go to the front I would have to say hello multiple times for somebody to come to the front to assist me. There was a guy on night shift with black glasses, would always say Jesus Christ or would mumble under his breath because it seemed like ..."
Reviewed on 29 May 2026
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is 3.481.210 ₫ per night from 3 Jun to 4 Jun
3.481.210 ₫
3.980.068 ₫ total
3 Jun - 4 Jun
includes taxes & fees
7.8/10 Good! (83 reviews)
"There is a pool but no life guard. The restaurant is closed. No breakfast. You have to make your own coffee. The room was clean but a little damp. Nobody in the office after 5. The beds were comfortable, the view of the sunset over the bay was fabulous. We got carry-out and ate at the outdoor seating. ..."
Reviewed on 28 May 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
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
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.
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.
