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Compare 531 Vacation Homes in Chestertown with updated reviews, rates, and availability.

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, (212)

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, (184)

Captivating Chesapeake experience
Captivating Chesapeake experience
10.0 out of 10, Exceptional, (259)

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
9.6 out of 10, Exceptional, (27)
The price is AED 251
AED 908 total
includes taxes & fees
28 Apr - 29 Apr

Historic Annapolis Home 1.5 blocks from center of town.
Historic Annapolis Home 1.5 blocks from center of town.
9.8 out of 10, Exceptional, (35)

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
10.0 out of 10, Exceptional, (51)

Entire House by the Fells Point, JHU.
Entire House by the Fells Point, JHU.
9.8 out of 10, Exceptional, (21)
The price is AED 455
AED 865 total
includes taxes & fees
27 Apr - 28 Apr

Steps to USNA Gate 3 at historic Gatehouse, on-site parking
Steps to USNA Gate 3 at historic Gatehouse, on-site parking
10.0 out of 10, Exceptional, (5)
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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Other property types in Chestertown

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

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, (212)

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, (23)
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

Best Western Kent Narrows Inn
5/5 Excellent
"The property was quiet and pet friendly. "
A verified traveler from Greensburg stayed at Best Western Kent Narrows Inn
Posted 1 day ago
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