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, 125 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
Cottage in Saint Michaels
4.98 out of 5 average rating, 142 reviewsLa Casita on Harris Creek, St. Michaels
Farm stay in Onancock
4.99 out of 5 average rating, 185 reviewsPrivate romantic pet friendly waterfront cottage
Cottage in Heathsville
4.94 out of 5 average rating, 184 reviewsHedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
Apartment in Lexington Park
4.97 out of 5 average rating, 515 reviewsHistoric St. Mary's City, MD
Guesthouse in White Stone
5.0 out of 5 average rating, 195 reviewsWaterfront Guesthouse II on the Rappahannock
Guest suite in Piney Point
4.94 out of 5 average rating, 229 reviewsSpectacular beachfront walk-out in Piney Point MD
Chesapeake Bay fishing vacation rentals
Apartment in Stevensville
4.98 out of 5 average rating, 246 reviewsBoutique by the Bay
Guest suite in Tilghman Island
4.97 out of 5 average rating, 116 reviewsBlack Walnut Cove Retreat, Tilghman Island
Cottage in Smith Island
4.97 out of 5 average rating, 192 reviewsLevering Creek Cottage with Private Docking
Guest suite in Lusby
4.99 out of 5 average rating, 310 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Tiny home in Cambridge
4.88 out of 5 average rating, 510 reviewsBlackwater Tiny Cabin on Snakehead Creek
Guest suite in Arnold
4.96 out of 5 average rating, 577 reviewsOld Bay Bungalow
Apartment in Frederica
4.97 out of 5 average rating, 265 reviewsSmokefree Lakeside Relaxation
Guest suite in Colonial Beach
4.97 out of 5 average rating, 275 reviewsBayview Bungalow
Chesapeake Bay house rentals
Home in Heathsville
4.94 out of 5 average rating, 129 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
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 Charles City
4.99 out of 5 average rating, 236 reviewsHutch's Bluff - Waterfront near Williamsburg
Home in Gloucester
4.96 out of 5 average rating, 137 reviewsBee Humble Cottage Entire Home
Home in Tracys Landing
4.99 out of 5 average rating, 172 reviewsThe Little Gypsy BoHome
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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