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Our pick of the best Chestertown Hotel Deals
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$141 per night from 22 May to 23 May
NZ$141
per night
22 May - 23 May
7.2/10 Good! (264 reviews)
"Hotel was a hotel… hated the small toilets… if you go to wipe your hand will end up touching the water.. yuck! If you’re a man and have to poop…. hold your junk up!!!"
Reviewed on 13 May 2024
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$226 per night from 16 May to 17 May
NZ$226
per night
16 May - 17 May
8.4/10 Very Good! (671 reviews)
"The onsite manager was very helpful. The staff was very nice."
Reviewed on 13 May 2024
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$322 per night from 28 May to 29 May
NZ$322
per night
28 May - 29 May
8.8/10 Excellent! (1,612 reviews)
"The location was excellent, the room wss very nice bit was decorated in a fashion that was too modern give the name of the hotel. The staff was friendly and efficient but said they would send an Anniversary present to our room but it never arrived. The facility was good but the elevator was too ..."
Reviewed on 9 May 2024
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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Discover the most popular places to visit in Chestertown
Washington College
Enjoy the student vibe when you visit Washington College during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
River Arts Chestertown
Enjoy the student vibe when you visit River Arts Chestertown during your trip to Chestertown. Take in the festivals in this family-friendly area.
More holiday ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.