Chestertown Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$134 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundable
The price is S$156 per night from 12 Apr to 13 Apr
S$156
12 Apr - 13 Apr
includes taxes & fees
8.6/10 Excellent! (890 reviews)
N/A
Reviewed on 20 Mar, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
9/10 Wonderful! (1,875 reviews)
Clean room, friendly staff, and the PERFECT location for walking downtown Annapolis.
Reviewed on 24 Mar, 2026
Hampton Inn Baltimore/Glen Burnie
6617 Ritchie Hwy Glen Burnie MD
Fully refundableReserve now, pay when you stay
The price is S$136 per night from 5 Apr to 6 Apr
S$136
5 Apr - 6 Apr
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
Nice clean rooms and staff. Good location
Reviewed on 25 Mar, 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.
Explore a world of travel with Expedia
* 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.
