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 refundable
The price is NZ$205 per night from 14 June to 15 June
NZ$205
14 June - 15 June
includes taxes & fees
8.6/10 Excellent! (913 reviews)
"I called the central reservation desk to extend my stay at 08000 the morning of check-in. They verified the reservation under the current ID was extended. When I confirmed this with the front desk, she said they were no rooms available. There was no discussion and she and the next clerk gave no explanation. ..."
Reviewed on 19 May 2026
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is NZ$136 per night from 28 May to 29 May
NZ$136
28 May - 29 May
includes taxes & fees
7.2/10 Good! (441 reviews)
"This hotel is in need of repair. The pull out sofa had more rips and tears than what should ever be seen. Way over priced for what you get"
Reviewed on 19 May 2026
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is NZ$246 per night from 3 June to 4 June
NZ$246
3 June - 4 June
includes taxes & fees
8/10 Very Good! (82 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again"
Reviewed on 18 May 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.
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.
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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.
