Chestertown Holidays
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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$143 per night from 1 Mar to 2 Mar
S$143
1 Mar - 2 Mar
includes taxes & fees
8.4/10 Very Good! (871 reviews)
Polite and kind hotel manager
Reviewed on 25 Jan, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,885 reviews)
Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!
Reviewed on 31 Jan, 2026
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
Fully refundableReserve now, pay when you stay
The price is S$92 per night from 17 Feb to 18 Feb
S$92
17 Feb - 18 Feb
includes taxes & fees
7/10 Good! (1,154 reviews)
Very nice stay, staff was very understanding and breakfast was amazing. Room was clean and we had no problems.
Reviewed on 4 Feb, 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.
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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.
