Holiday rentals in Chesapeake Bay
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Top-rated holiday rentals in Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake Bay holiday rentals
Other great holiday rentals in Chesapeake Bay
Guest favourite
Tiny home in Saint Inigoes
Historic St.Mary's City at the Lazy Bear Cottage
Guest favourite
Cottage in Saint Michaels
La Casita on Harris Creek, St. Michaels
Guest favourite
Cottage in Onancock
Escape to the Eastern Shore - Upscale w dock
Guest favourite
Farm stay in Cardinal
Wtrfrnt aptmnt w/pool/dock on private farm
Guest favourite
Farm stay in Onancock
Private romantic pet friendly waterfront cottage
Guest favourite
Rental unit in Stevensville
Boutique by the Bay
Guest favourite
Tiny home in Machipongo
Machipongo Glamper
Guest favourite
Home in Chestertown
Waterfront house with private dock & kayaks!
Destinations to explore
- Yurt Rentals United States
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