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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, (215)

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, (186)

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 424
AED 1,096 total
includes taxes & fees
18 May - 19 May

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, (53)

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 617
AED 1,090 total
includes taxes & fees
11 May - 12 May

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, (215)

BAYSIDE BUNGALOW
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (35)
The price is AED 643
AED 997 total
includes taxes & fees
11 May - 12 May
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

Hyatt Place Kent Narrows & Marina
5/5 Excellent
Gorgeous Water view
"The room was lovely with a gorgeous view of the Harbor. The breakfast buffet was quite nice.
Easy walking distance to at least 5 restaurants. Staff was friendly and knowledgeable in helping us with all of our needs"
A verified traveler stayed at Hyatt Place Kent Narrows & Marina
Posted 14 hours ago
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