Crumpton
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Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is CA $103 per night from Oct 18 to Oct 19
CA $103
CA $114 total
Oct 18 - Oct 19
includes taxes & fees
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
Quality Inn Smyrna
190 Stadium St, Gateway North Plaza Smyrna DE
The price is CA $120 per night from Nov 10 to Nov 11
CA $120
CA $133 total
Nov 10 - Nov 11
includes taxes & fees
Book a stay at this business-friendly hotel in Smyrna. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
The price is CA $154 per night from Oct 14 to Oct 15
CA $154
CA $176 total
Oct 14 - Oct 15
includes taxes & fees
Book a stay at this beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point ...
8/10 Very good! (119 reviews)
"Stayed in October. Room was clean and had a great view of the water. No microwave or coffee in the room but it was always available at the end of the hall. Keyless entry was convenient . Cell service is terrible though had to go to the windows to have any service."
Reviewed on Oct 12, 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.
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Rock Hall MD
Book a stay at this family-friendly villa in Rock Hall. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Rock Hall Harbor and The Mainstay ...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Earleville MD
Stay at this cottage in Earleville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Turkey Point Light and Elk Neck State Park are located ...
9.8/10 Exceptional! (72 reviews)
"We had a wonderful long weekend at the cottage. It is beautifully decorated and very clean. It was perfect for our needs. We spent our days boating on the upper bay (gorgeous weather) and evenings relaxing on the deck with a perfect view of the sunset and turkey point lighthouse. Thank you Chris ..."
Reviewed on Sep 1, 2026
First Floor Studio Apartment in Historic Chestertown
Chestertown MD
Book a stay at this golf apartment in Chestertown. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Wilmer Park and Sumner Hall are ...
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.
