Chestertown Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Patricia Knorr
Top hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundableReserve now, pay when you stay
The price is 2.621.084 ₫ per night from 1 Feb to 2 Feb
2.621.084 ₫
2.909.404 ₫ total
1 Feb - 2 Feb
includes taxes & fees
8.4/10 Very Good! (863 reviews)
Very nice
Reviewed on 14 Dec 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is 1.891.152 ₫ per night from 17 Jan to 18 Jan
1.891.152 ₫
2.099.179 ₫ total
17 Jan - 18 Jan
includes taxes & fees
7.2/10 Good! (426 reviews)
Clean and friendly staff. Good location.
Reviewed on 2 Jan 2026
Pendry Baltimore
1715 Thames St. Baltimore MD
Fully refundableReserve now, pay when you stay
The price is 8.405.120 ₫ per night from 29 Jan to 30 Jan
8.405.120 ₫
10.956.337 ₫ total
29 Jan - 30 Jan
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
The hotel was beautiful, and the staff was courteous and friendly.
Reviewed on 5 Jan 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.
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.
