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 2.688.006 ₫ per night from 23 Nov to 24 Nov
2.688.006 ₫
2.983.687 ₫ total
23 Nov - 24 Nov
includes taxes & fees
8.4/10 Very Good! (848 reviews)
Good location. Very pricey but not much competition
Reviewed on 17 Nov 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is 1.897.416 ₫ per night from 30 Nov to 1 Dec
1.897.416 ₫
2.106.132 ₫ total
30 Nov - 1 Dec
includes taxes & fees
7.2/10 Good! (414 reviews)
This property was clean but dated. The carpet was stained, the furniture and fixtures were worn and broken, towels were washed but old and in need of replacement.
Reviewed on 9 Nov 2025
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is 2.608.947 ₫ per night from 20 Nov to 21 Nov
2.608.947 ₫
2.982.809 ₫ total
20 Nov - 21 Nov
includes taxes & fees
7.8/10 Good! (75 reviews)
Beautiful view
Reviewed on 8 Nov 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.
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.
