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
Home in Chestertown
4.94 out of 5 average rating, 128 reviewsCHESAPEAKE SUNSETS
4–11 May
€ 212 per night
Guest favourite
Guest house in Stevensville
5.0 out of 5 average rating, 207 reviewsWaterfront Getaway - View of bay from your bed
25 Sep – 2 Oct
€ 289 per night
Guest favourite
Cabin in Deltaville
4.97 out of 5 average rating, 253 reviews"The Little Red Cabin" aka The Galley
16–23 Nov
€ 116 per night
Guest favourite
Home in Heathsville
4.93 out of 5 average rating, 122 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
16–23 Nov
€ 397 per night
Guest favourite
Farm stay in Cardinal
4.95 out of 5 average rating, 108 reviewsWtrfrnt aptmnt w/pool/dock on private farm
20–27 Nov
€ 150 per night
Guest favourite
Guest suite in Chincoteague
4.93 out of 5 average rating, 224 reviewsBaywatch North-Waterfront & Roaming Ponies
21–28 Oct
€ 117 per night
Guest favourite
Cottage in Heathsville
4.94 out of 5 average rating, 178 reviewsHedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
14–21 Sep
€ 134 per night
Guest favourite
Casa particular in Chestertown
4.93 out of 5 average rating, 102 reviewsRed, White & Waterview Studio Apt with pool
12–19 Jan
€ 139 per night
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