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 Cardinal
4.91 out of 5 average rating, 117 reviewsWtrfrnt aptmnt w/pool/dock on private farm
Cottage in Onancock
4.97 out of 5 average rating, 202 reviewsEscape to the Eastern Shore - Upscale w dock
Guest suite in Piney Point
4.94 out of 5 average rating, 228 reviewsSpectacular beachfront walk-out in Piney Point MD
Home in Reedville
4.98 out of 5 average rating, 124 reviewsSunkissed Cottage-private, natural waterfront home
Apartment in Lexington Park
4.97 out of 5 average rating, 514 reviewsHistoric St. Mary's City, MD
Cottage in Leonardtown
4.96 out of 5 average rating, 131 reviewsBeach Front and 'Perfectly Placed'
Tiny home in Cape Charles
4.98 out of 5 average rating, 278 reviewsThe Laughing King Retreat Honeymoon Island Cottage
Apartment in North
4.97 out of 5 average rating, 196 reviewsLittle Cove Cottage, Couples Retreat/Mathews
Chesapeake Bay fishing vacation rentals
Apartment in Stevensville
4.98 out of 5 average rating, 244 reviewsBoutique by the Bay
Cottage in Heathsville
4.94 out of 5 average rating, 181 reviewsHedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
Guest suite in Colonial Beach
4.97 out of 5 average rating, 272 reviewsBayview Bungalow
Tiny home in Cambridge
4.89 out of 5 average rating, 508 reviewsBlackwater Tiny Cabin on Snakehead Creek
Cabin in Lusby
4.91 out of 5 average rating, 215 reviewsPeaceful Waterfront Retreat on The Bay
Guesthouse in Saluda
4.93 out of 5 average rating, 475 reviewsWooded Cabin retreat on fresh water pond
Guesthouse in Church Road
5.0 out of 5 average rating, 139 reviewsHeron Rock: Lakefront Cottage on Lake Chesdin
Tiny home in Deltaville
4.98 out of 5 average rating, 115 reviewsVirginia Dare
Chesapeake Bay home rentals
Home in Lusby
5.0 out of 5 average rating, 114 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
Home in Reedville
4.96 out of 5 average rating, 206 reviewsWaterfront FamilyFriendly Home Improved for 2023
Home in Gloucester
4.96 out of 5 average rating, 137 reviewsBee Humble Cottage Entire Home
Home in Stevensville
5.0 out of 5 average rating, 104 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Home in Chestertown
5.0 out of 5 average rating, 157 reviewsNicely refurbished historic house near town center
Home in Charles City
4.99 out of 5 average rating, 235 reviewsHutch's Bluff - Waterfront near Williamsburg
Home in Shady Side
5.0 out of 5 average rating, 121 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Home in Chincoteague
4.94 out of 5 average rating, 304 reviewsSeas the Day Getaway~Pool ~near Waterfront Park
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