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
Get the amount of space that is right for you
Popular amenities for Chesapeake Bay vacation rentals
Chesapeake Bay waterfront vacation rentals
Farm stay in Cardinal
4.91 out of 5 average rating, 121 reviewsWtrfrnt aptmnt w/pool/dock on private farm
Tiny home in Saint Inigoes
4.98 out of 5 average rating, 301 reviewsHistoric St.Mary's City at the Lazy Bear Cottage
Farm stay in Onancock
4.99 out of 5 average rating, 184 reviewsPrivate romantic pet friendly waterfront cottage
Cottage in Saint Michaels
4.98 out of 5 average rating, 142 reviewsLa Casita on Harris Creek, St. Michaels
Cottage in Leonardtown
4.96 out of 5 average rating, 131 reviewsBeach Front and 'Perfectly Placed'
Guest suite in Piney Point
4.94 out of 5 average rating, 229 reviewsSpectacular beachfront walk-out in Piney Point MD
Apartment in North
4.97 out of 5 average rating, 197 reviewsLittle Cove Cottage, Couples Retreat/Mathews
Guesthouse in White Stone
5.0 out of 5 average rating, 195 reviewsWaterfront Guesthouse II on the Rappahannock
Chesapeake Bay fishing vacation rentals
Apartment in Stevensville
4.98 out of 5 average rating, 246 reviewsBoutique by the Bay
Guest suite in Colonial Beach
4.97 out of 5 average rating, 275 reviewsBayview Bungalow
Tiny home in Deltaville
4.98 out of 5 average rating, 115 reviewsVirginia Dare
Cabin in Lusby
4.91 out of 5 average rating, 215 reviewsPeaceful Waterfront Retreat on The Bay
Tiny home in Cambridge
4.88 out of 5 average rating, 510 reviewsBlackwater Tiny Cabin on Snakehead Creek
Guest suite in Tilghman Island
4.97 out of 5 average rating, 116 reviewsBlack Walnut Cove Retreat, Tilghman Island
Guest suite in Lusby
4.99 out of 5 average rating, 310 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Guest suite in Arnold
4.96 out of 5 average rating, 577 reviewsOld Bay Bungalow
Chesapeake Bay home rentals
Home in Reedville
4.96 out of 5 average rating, 209 reviewsWaterfront FamilyFriendly Home Improved for 2023
Home in Lusby
5.0 out of 5 average rating, 114 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
Home in Stevensville
5.0 out of 5 average rating, 105 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Home in TYLERTON
4.95 out of 5 average rating, 119 reviews3 bedroom/2.5 bath Smith Island bungalow with dock
Home in Stevensville
4.97 out of 5 average rating, 100 reviewsThe Kent Island House
Home in Gloucester
4.96 out of 5 average rating, 137 reviewsBee Humble Cottage Entire Home
Home in Lusby
4.98 out of 5 average rating, 266 reviewsCove Point Beach Cabin
Home in Tangier
4.98 out of 5 average rating, 142 reviewsWatermans Hideaway, Tangier Island, Chesapeake Bay
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