Chestertown Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥85,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Find the Best Chestertown Vacation Packages
Chestertown Hotel Deals
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundable
The price is ￥19,108 per night from May 26 to May 27
￥19,108
￥21,210 total
May 26 - May 27
includes taxes & fees
8.6/10 Excellent! (905 reviews)
Will at the front desk might be one of the worst hotel people I’ve ever had to deal with
Reviewed on Apr 26, 2026
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is ￥16,869 per night from Apr 29 to Apr 30
￥16,869
￥19,286 total
Apr 29 - Apr 30
includes taxes & fees
7.8/10 Good! (80 reviews)
A lovely spot with views of the marina. We went in the offseason, so there were very few hotel guests and the price was extremely reasonable. Memory foam mattresses. Nothing fancy, but it had a small fridge and free coffee from a station in the hall. Note: no elevator, so if mobility is an issue, ...
Reviewed on Apr 23, 2026
Blue Heron Farm Waterfront Chalet
Chestertown MD
10/10 Exceptional! (2 reviews)
Location! Location!
Reviewed on Jan 22, 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
