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 refundableReserve now, pay when you stay
The price is 2.635.767 ₫ per night from 8 Mar to 9 Mar
2.635.767 ₫
2.925.702 ₫ total
8 Mar - 9 Mar
includes taxes & fees
8.6/10 Excellent! (879 reviews)
I reserved a suite for two nights on 12/26/25. Almost 2 months in advance. When I arrived the check-in girl said that she downgraded my room to a double because they were overbooked and since I only two people in my group she gave my suite to a party with 4 people because they needed more room than ...
Reviewed on 17 Feb 2026
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
Fully refundableReserve now, pay when you stay
The price is 1.855.330 ₫ per night from 16 Mar to 17 Mar
1.855.330 ₫
2.142.906 ₫ total
16 Mar - 17 Mar
includes taxes & fees
7/10 Good! (1,168 reviews)
The room itself was in good condition overall, but the sink was dirty, the bedding was stained upon arrival, which was disappointing. Housekeeping did not automatically service the room—I had to request cleaning, and towels otherwise it would not have been done. I was placed on a floor that appeared ...
Reviewed on 28 Feb 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,877 reviews)
Such a cool place to stay! Water pressure wasn’t great but it’s a very old building.
Reviewed on 26 Feb 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
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.
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.
