Chestertown Packages (Flight + Hotel)
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Top hotels in Chestertown
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is ฿2,620 per night from 13 Oct to 14 Oct
฿2,620
฿2,908 total
13 Oct - 14 Oct
includes taxes & fees
7.2/10 Good! (398 reviews)
"Room temperature was good. Room was also very spacious and clean."
Reviewed on 27 Sept 2025
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is ฿3,726 per night from 2 Nov to 3 Nov
฿3,726
฿4,136 total
2 Nov - 3 Nov
includes taxes & fees
8.4/10 Very Good! (825 reviews)
"Nice hotel"
Reviewed on 29 Sept 2025
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is ฿4,279 per night from 8 Oct to 9 Oct
฿4,279
฿4,892 total
8 Oct - 9 Oct
includes taxes & fees
7.8/10 Good! (70 reviews)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"
Reviewed on 5 Sept 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
