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Compare 441 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, (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)

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)

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (104)

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
10.0 out of 10, Exceptional, (85)

Historic Annapolis Home 1.5 blocks from center of town.
Historic Annapolis Home 1.5 blocks from center of town.
10.0 out of 10, Exceptional, (34)

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
9.8 out of 10, Exceptional, (11)

Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD
Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD
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

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)

Captivating Chesapeake experience
Captivating Chesapeake experience
10.0 out of 10, Exceptional, (257)
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

Hilton Garden Inn Baltimore/White Marsh
5/5 Excellent
Nice place to stay
"Everything was pleasant and peaceful, the staff was very helpful, my only suggestions are the television was out dated, no Netflix and there were no blinds or curtains to keep the lights out"
A verified traveler stayed at Hilton Garden Inn Baltimore/White Marsh
Posted 18 hours ago
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