Chestertown Holidays
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Save up to Rp173.195 when you book a flight and hotel together*
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Top hotels in Chestertown
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is Rp1.264.167 per night from 28 Sept to 29 Sept
Rp1.264.167
Rp1.403.225 total
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 Rp1.917.628 per night from 28 Sept to 29 Sept
Rp1.917.628
Rp2.128.566 total
28 Sept - 29 Sept
includes taxes & fees
8.4/10 Very Good! (817 reviews)
"Smells like an air freshener. That is annoying. The beds re lovely"
Reviewed on 17 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 Rp2.186.522 per night from 21 Sept to 22 Sept
Rp2.186.522
Rp2.427.039 total
21 Sept - 22 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.
Popular places to visit
Wilmer Park
Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.
Crumpton Auction
Take the family on an outing to Crumpton Auction during your trip to Chestertown. Take in the festivals while you're in the area.
More trip options
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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.
