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, 118 reviewsWtrfrnt aptmnt w/pool/dock on private farm
Farm stay in Cape Charles
5.0 out of 5 average rating, 337 reviewsPrivate Guesthouse on Secluded Waterfront Farm
Apartment in Lexington Park
4.97 out of 5 average rating, 515 reviewsHistoric St. Mary's City, MD
Home in Reedville
4.98 out of 5 average rating, 124 reviewsSunkissed Cottage-private, natural waterfront home
Home in Cape Charles
4.99 out of 5 average rating, 105 reviewsModern Private Beach House close to Cape Charles
Cottage in Saint Michaels
4.98 out of 5 average rating, 141 reviewsLa Casita on Harris Creek, St. Michaels
Tiny home in Accomac
4.93 out of 5 average rating, 444 reviewsLittle Red House on a Farm - Quiet Rural Waterview
Guesthouse in Yorktown
4.97 out of 5 average rating, 209 reviewsCharming Yorktown Battlefield Cottage
Chesapeake Bay fishing vacation rentals
Tiny home in Cape Charles
4.98 out of 5 average rating, 278 reviewsThe Laughing King Retreat Honeymoon Island Cottage
Guest suite in Piney Point
4.94 out of 5 average rating, 229 reviewsSpectacular beachfront walk-out in Piney Point MD
Cabin in Lusby
4.91 out of 5 average rating, 215 reviewsPeaceful Waterfront Retreat on The Bay
Apartment in Stevensville
4.98 out of 5 average rating, 246 reviewsBoutique by the Bay
Guesthouse in Gloucester
5.0 out of 5 average rating, 111 reviewsCreekside Guesthouse - Dock and Pool on 10 acres
Tiny home in Cambridge
4.88 out of 5 average rating, 510 reviewsBlackwater Tiny Cabin on Snakehead Creek
Guest suite in Colonial Beach
4.97 out of 5 average rating, 275 reviewsBayview Bungalow
Guest suite in Lusby
4.99 out of 5 average rating, 310 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Chesapeake Bay home rentals
Home in Reedville
4.96 out of 5 average rating, 209 reviewsWaterfront FamilyFriendly Home Improved for 2023
Home in Heathsville
4.94 out of 5 average rating, 126 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
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 Cambridge
4.92 out of 5 average rating, 183 reviewsGuest House: Farm homestead
Home in Annapolis
4.96 out of 5 average rating, 116 reviewsHistoric Downtown in-law suite
Home in Chincoteague
4.94 out of 5 average rating, 305 reviewsSeas the Day Getaway~Pool ~near Waterfront Park
Home in TYLERTON
4.95 out of 5 average rating, 119 reviews3 bedroom/2.5 bath Smith Island bungalow with dock
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