Chesapeake Bay vacation rentals
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Top-rated vacation rentals in Chesapeake Bay
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Chesapeake Bay vacation rentals
Chesapeake Bay waterfront vacation rentals
Farm stay in Onancock
4.99 out of 5 average rating, 186 reviewsPrivate romantic pet friendly waterfront cottage
Farm stay in Cape Charles
5 out of 5 average rating, 341 reviewsPrivate Guesthouse on Secluded Waterfront Farm
Cottage in Onancock
4.97 out of 5 average rating, 203 reviewsEscape to the Eastern Shore - Upscale w dock
Home in Reedville
4.98 out of 5 average rating, 126 reviewsSunkissed Cottage-private, natural waterfront home
Cottage in Saint Michaels
4.97 out of 5 average rating, 143 reviewsLa Casita on Harris Creek, St. Michaels
Cottage in Heathsville
4.94 out of 5 average rating, 185 reviewsHedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
Rental unit in Lexington Park
4.97 out of 5 average rating, 516 reviewsHistoric St. Mary's City, MD
Guest suite in Piney Point
4.94 out of 5 average rating, 230 reviewsSpectacular beachfront walk-out in Piney Point MD
Chesapeake Bay fishing vacation rentals
Rental unit in Stevensville
4.98 out of 5 average rating, 247 reviewsBoutique by the Bay
Guest suite in Lusby
4.99 out of 5 average rating, 310 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Guest suite in Tilghman Island
4.97 out of 5 average rating, 117 reviewsBlack Walnut Cove Retreat, Tilghman Island
Guesthouse in Saluda
4.93 out of 5 average rating, 480 reviewsWooded Cabin retreat on fresh water pond
Cabin in Lusby
4.91 out of 5 average rating, 216 reviewsPeaceful Waterfront Retreat on The Bay
Rental unit in Frederica
4.97 out of 5 average rating, 266 reviewsSmokefree Lakeside Relaxation
Tiny home in Cambridge
4.88 out of 5 average rating, 513 reviewsBlackwater Tiny Cabin on Snakehead Creek
Guesthouse in Church Road
5 out of 5 average rating, 145 reviewsHeron Rock: Lakefront Cottage on Lake Chesdin
Chesapeake Bay house rentals
Home in Stevensville
5 out of 5 average rating, 105 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Home in Reedville
4.96 out of 5 average rating, 209 reviewsWaterfront FamilyFriendly Home Improved for 2023
Home in Lusby
5 out of 5 average rating, 116 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
Home in Lusby
4.98 out of 5 average rating, 266 reviewsCove Point Beach Cabin
Home in Crisfield
4.95 out of 5 average rating, 259 reviewsCozy Home near Waterfront in Crisfield, MD
Home in TYLERTON
4.95 out of 5 average rating, 120 reviews3 bedroom/2.5 bath Smith Island bungalow with dock
Home in Chestertown
5 out of 5 average rating, 159 reviewsNicely refurbished historic house near town center
Home in Gloucester
4.96 out of 5 average rating, 138 reviewsBee Humble Cottage Entire Home
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