Chestertown Holidays
Photo by Patricia Knorr
- Plan, book, travel with confidence
Better together
Save up to S$134 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top hotels in Chestertown
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is S$109 per night from 28 Sept to 29 Sept
S$109
28 Sept - 29 Sept
includes taxes & fees
7.2/10 Good! (395 reviews)
"Time to upgrade the furniture in the rooms. The staff is doing a GREAT JOB cleaning and providing excellent service."
Reviewed on 1 Sept, 2025
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is S$165 per night from 28 Sept to 29 Sept
S$165
28 Sept - 29 Sept
includes taxes & fees
8.4/10 Very Good! (819 reviews)
"Great property"
Reviewed on 21 Sept, 2025
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is S$189 per night from 24 Sept to 25 Sept
S$189
24 Sept - 25 Sept
includes taxes & fees
8/10 Very Good! (68 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.
* 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.
