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 29 Dec to 30 Dec
S$148
29 Dec - 30 Dec
includes taxes & fees
8.4/10 Very Good! (861 reviews)
Very nice
Reviewed on 14 Dec, 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is S$103 per night from 31 Dec to 1 Jan
S$103
31 Dec - 1 Jan, 2026
includes taxes & fees
7.2/10 Good! (421 reviews)
Very clean. Pets allowed.
Reviewed on 14 Dec, 2025
Pendry Baltimore
1715 Thames St. Baltimore MD
Fully refundableReserve now, pay when you stay
The price is S$530 per night from 22 Jan to 23 Jan
S$530
22 Jan - 23 Jan, 2026
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Really nice cozy room we had the terrace balcony would definitely stay again!
Reviewed on 9 Dec, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
