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Compare 54 Cottages in Chestertown with updated reviews, rates, and availability.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (45)

Waterfront dog-friendly home with beach just mins to Downtown Annapolis
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
9.8 out of 10, Exceptional, (29)

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
9.8 out of 10, Exceptional, (22)

Peaceful getaway convenient to local amenities including beach, boating & food
Peaceful getaway convenient to local amenities including beach, boating & food
9.8 out of 10, Exceptional, (110)

Amazing views, short walks to great dining!
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (78)

Secluded Waterfront Cottage on 200 acre farm near Queenstown
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (97)

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
10.0 out of 10, Exceptional, (26)

The Heron's Nest at Atlantic Marina
The Heron's Nest at Atlantic Marina
10.0 out of 10, Exceptional, (286)
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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Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (209)

240' Private Beachfront @Kent Island Love Point - Great for Large Groups
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
10.0 out of 10, Exceptional, (180)

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.4 out of 10, Exceptional, (22)
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.
Recent reviews of Chestertown hotels
Recent reviews of Chestertown hotels

Historic Inns of Annapolis
5/5 Excellent
"Great hotel. "
A verified traveler stayed at Historic Inns of Annapolis
Posted 5 hours ago
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