Chestertown Vacations
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Find the Best Chestertown Vacation Packages
Chestertown Hotel Deals
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundableReserve now, pay when you stay
The price is ₩148,297 per night from Nov 20 to Nov 21
₩148,297
₩164,610 total
Nov 20 - Nov 21
includes taxes & fees
8.4/10 Very Good! (845 reviews)
Very clean hotel. Perfect if you have to do work at Washington College
Reviewed on Nov 12, 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is ₩104,680 per night from Nov 30 to Dec 1
₩104,680
₩116,194 total
Nov 30 - Dec 1
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 Nov 9, 2025
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
Fully refundable
The price is ₩143,935 per night from Nov 17 to Nov 18
₩143,935
₩164,560 total
Nov 17 - Nov 18
includes taxes & fees
7.8/10 Good! (75 reviews)
Beautiful view
Reviewed on Nov 8, 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.
Discover the most popular places to visit in Chestertown
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
