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 2.913.773 ₫ per night from 26 Apr to 27 Apr
2.913.773 ₫
3.234.287 ₫ total
26 Apr - 27 Apr
includes taxes & fees
8.6/10 Excellent! (898 reviews)
The room was very clean but smelled as if someone had smoked in the room. Parlikg area was not well lighted and not welcoming.
Reviewed on 12 Apr 2026
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is 2.844.504 ₫ per night from 19 Apr to 20 Apr
2.844.504 ₫
3.252.123 ₫ total
19 Apr - 20 Apr
includes taxes & fees
7.8/10 Good! (77 reviews)
I was unaware that this hotel was a seasonal place to stay. When we arrived the place was a ghosttown. The two employees i
Reviewed on 8 Dec 2025
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is 4.006.010 ₫ per night from 19 Apr to 20 Apr
4.006.010 ₫
5.467.769 ₫ total
19 Apr - 20 Apr
includes taxes & fees
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.
