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
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Popular amenities for Chesapeake Bay holiday rentals
Other great holiday rentals in Chesapeake Bay
Guest favourite
Cottage in Westover
4.99 out of 5 average rating, 183 reviewsRumbley Cottage on the Tangier Sound-Private Beach
Guest favourite
Campervan/Motorhome in Chestertown
4.89 out of 5 average rating, 124 reviewsCozy Airstream on a beautiful horse farm
Guest favourite
Tiny home in Machipongo
4.98 out of 5 average rating, 260 reviewsMachipongo Glamper
Guest favourite
Guest suite in Piney Point
4.94 out of 5 average rating, 225 reviewsSpectacular beachfront walk-out in Piney Point MD
Guest favourite
Flat in Stevensville
4.98 out of 5 average rating, 242 reviewsBoutique by the Bay
Guest favourite
Casa particular in Chestertown
4.93 out of 5 average rating, 103 reviewsRed, White & Waterview Studio Apt with pool
Guest favourite
Home in Heathsville
4.93 out of 5 average rating, 122 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
Guest favourite
Cottage in Smith Island
4.97 out of 5 average rating, 187 reviewsLevering Creek Cottage with Private Docking
Destinations to explore
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