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
Farm stay in Onancock
4.99 out of 5 average rating, 177 reviewsPrivate romantic pet friendly waterfront cottage
27 Sep – 4 Oct
₹15,157 per night
Guest favourite
Farm stay in Madison
4.98 out of 5 average rating, 164 reviewsMadison Nature Getaway
20–27 Dec
₹11,708 per night
Guest favourite
Campervan/Motorhome in Chestertown
4.89 out of 5 average rating, 124 reviewsCozy Airstream on a beautiful horse farm
7–14 Oct
₹11,082 per night
Guest favourite
Guest house in Easton
4.99 out of 5 average rating, 547 reviewsChill in The Crib! Easton, Maryland
24–29 Aug
₹13,698 per night
Guest favourite
Casa particular in Chestertown
4.93 out of 5 average rating, 103 reviewsRed, White & Waterview Studio Apt with pool
28 Mar – 4 Apr
₹11,573 per night
Guest favourite
Tiny home in Cambridge
4.99 out of 5 average rating, 159 reviewsBlackwater Refuge House on The Farm, water access
10–17 Sep
₹9,114 per night
Guest favourite
Cottage in Heathsville
4.94 out of 5 average rating, 180 reviewsHedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
7–14 Sep
₹10,433 per night
Guest favourite
Cottage in Smith Island
4.97 out of 5 average rating, 186 reviewsLevering Creek Cottage with Private Docking
24–31 Oct
₹14,623 per night
Destinations to explore
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