Chestertown Holidays
Photo by Patricia Knorr
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Top hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is S$148 per night from 16 Nov to 17 Nov
S$148
16 Nov - 17 Nov
includes taxes & fees
8.4/10 Very Good! (838 reviews)
This property is clean and welcoming. We were pleasantly surprised. Check in was easy, and the room was great. Breakfast was wonderful! Great place to stay.
Reviewed on 2 Nov, 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is S$104 per night from 30 Nov to 1 Dec
S$104
30 Nov - 1 Dec
includes taxes & fees
7.2/10 Good! (409 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 S$148 per night from 9 Nov to 10 Nov
S$148
9 Nov - 10 Nov
includes taxes & fees
7.8/10 Good! (73 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.
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