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 Rp1.355.778 per night from 5 Oct to 6 Oct
Rp1.355.778
Rp1.504.914 total
5 Oct - 6 Oct
includes taxes & fees
7.2/10 Good! (396 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 Rp1.929.820 per night from 29 Sept to 30 Sept
Rp1.929.820
Rp2.142.101 total
29 Sept - 30 Sept
includes taxes & fees
8.4/10 Very Good! (820 reviews)
Clean and quiet
"Nicely appointed with plenty of towels, and easy to operate TV and A/C."
Reviewed on 23 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 Rp2.214.437 per night from 27 Oct to 28 Oct
Rp2.214.437
Rp2.458.025 total
27 Oct - 28 Oct
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.
