Chestertown Holidays
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Chestertown Holiday
Our pick of the best Chestertown Hotel Deals
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$156 per night from 6 Oct to 7 Oct
NZ$156
6 Oct - 7 Oct
includes taxes & fees
7.2/10 Good! (396 reviews)
"Time to upgrade the furniture in the rooms. The staff is doing a GREAT JOB cleaning and providing excellent service."
Reviewed on 1 Sept 2025
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$225 per night from 30 Oct to 31 Oct
NZ$225
30 Oct - 31 Oct
includes taxes & fees
8.4/10 Very Good! (820 reviews)
Clean and quiet
"Nicely appointed with plenty of towels, and easy to operate TV and A/C."
Reviewed on 23 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 NZ$254 per night from 30 Sept to 1 Oct
NZ$254
30 Sept - 1 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.
Discover the most popular places to visit in Chestertown
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.
More holiday ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
