Chestertown Holidays
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Chestertown Holiday
Our pick of the best Chestertown Hotel Deals
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$194 per night from 16 Nov to 17 Nov
NZ$194
16 Nov - 17 Nov
includes taxes & fees
8.4/10 Very Good! (843 reviews)
Large clean room. Bed firm
Reviewed on 8 Nov 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$141 per night from 15 Dec to 16 Dec
NZ$141
15 Dec - 16 Dec
includes taxes & fees
7.2/10 Good! (411 reviews)
its an average hotel with a clean bed to sleep in
Reviewed on 28 Oct 2025
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
Fully refundable
The price is NZ$194 per night from 16 Nov to 17 Nov
NZ$194
16 Nov - 17 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.
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.
