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 Saint Michaels
4.98 out of 5 average rating, 141 reviewsLa Casita on Harris Creek, St. Michaels
Home in Cape Charles
4.99 out of 5 average rating, 105 reviewsModern Private Beach House close to Cape Charles
Home in Reedville
4.98 out of 5 average rating, 124 reviewsSunkissed Cottage-private, natural waterfront home
Guesthouse in White Stone
5.0 out of 5 average rating, 191 reviewsWaterfront Guesthouse II on the Rappahannock
Cottage in Leonardtown
4.96 out of 5 average rating, 131 reviewsBeach Front and 'Perfectly Placed'
Cabin in Lusby
4.91 out of 5 average rating, 215 reviewsPeaceful Waterfront Retreat on The Bay
Apartment in Lexington Park
4.97 out of 5 average rating, 514 reviewsHistoric St. Mary's City, MD
Chesapeake Bay fishing vacation rentals
Loft in Cape May Court House
4.97 out of 5 average rating, 594 reviewsQuiet Lakefront Studio - Close to the Beach
Guest suite in Piney Point
4.94 out of 5 average rating, 228 reviewsSpectacular beachfront walk-out in Piney Point MD
Guest suite in Colonial Beach
4.97 out of 5 average rating, 272 reviewsBayview Bungalow
Cottage in Smith Island
4.97 out of 5 average rating, 191 reviewsLevering Creek Cottage with Private Docking
Guest suite in Tilghman Island
4.97 out of 5 average rating, 115 reviewsBlack Walnut Cove Retreat, Tilghman Island
Tiny home in Cambridge
4.89 out of 5 average rating, 508 reviewsBlackwater Tiny Cabin on Snakehead Creek
Guesthouse in Church Road
5.0 out of 5 average rating, 139 reviewsHeron Rock: Lakefront Cottage on Lake Chesdin
Guest suite in Lusby
4.99 out of 5 average rating, 307 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Chesapeake Bay home rentals
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 Heathsville
4.94 out of 5 average rating, 124 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
Home in Annapolis
4.96 out of 5 average rating, 116 reviewsHistoric Downtown in-law suite
Home in Lusby
4.98 out of 5 average rating, 265 reviewsCove Point Beach Cabin
Home in Cambridge
4.92 out of 5 average rating, 183 reviewsGuest House: Farm homestead
Home in Charles City
4.99 out of 5 average rating, 235 reviewsHutch's Bluff - Waterfront near Williamsburg
Home in Chincoteague
4.94 out of 5 average rating, 304 reviewsSeas the Day Getaway~Pool ~near Waterfront Park
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