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
Home in Reedville
4.98 out of 5 average rating, 124 reviewsSunkissed Cottage-private, natural waterfront home
Cottage in Onancock
4.97 out of 5 average rating, 203 reviewsEscape to the Eastern Shore - Upscale w dock
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
Cottage in Leonardtown
4.96 out of 5 average rating, 131 reviewsBeach Front and 'Perfectly Placed'
Farm stay in Cardinal
4.91 out of 5 average rating, 117 reviewsWtrfrnt aptmnt w/pool/dock on private farm
Home in Heathsville
4.94 out of 5 average rating, 125 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
Tiny home in Accomac
4.93 out of 5 average rating, 444 reviewsLittle Red House on a Farm - Quiet Rural Waterview
Chesapeake Bay fishing vacation rentals
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, 245 reviewsBoutique by the Bay
Guest suite in Colonial Beach
4.97 out of 5 average rating, 275 reviewsBayview Bungalow
Tiny home in Cambridge
4.88 out of 5 average rating, 509 reviewsBlackwater Tiny Cabin on Snakehead Creek
Guesthouse in Gloucester
5.0 out of 5 average rating, 111 reviewsCreekside Guesthouse - Dock and Pool on 10 acres
Guesthouse in Saluda
4.93 out of 5 average rating, 478 reviewsWooded Cabin retreat on fresh water pond
Cabin in Lusby
4.94 out of 5 average rating, 150 reviewsHideaway on the Bay: Waterfront Vintage A Frame
Guest suite in Tilghman Island
4.97 out of 5 average rating, 115 reviewsBlack Walnut Cove Retreat, Tilghman Island
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, 104 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 Chestertown
5.0 out of 5 average rating, 157 reviewsNicely refurbished historic house near town center
Home in Gloucester
4.96 out of 5 average rating, 137 reviewsBee Humble Cottage Entire Home
Home in Charles City
4.99 out of 5 average rating, 235 reviewsHutch's Bluff - Waterfront near Williamsburg
Home in Tangier
4.98 out of 5 average rating, 142 reviewsWatermans Hideaway, Tangier Island, Chesapeake Bay
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