Chesapeake Bay vacation rentals
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Top-rated vacation rentals in Chesapeake Bay
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Popular amenities for Chesapeake Bay vacation rentals
Other great vacation rentals in Chesapeake Bay
Farm stay in Onancock
4.99 out of 5 average rating, 177 reviewsPrivate romantic pet friendly waterfront cottage
Sep 27 – Oct 4
Cottage in Heathsville
4.94 out of 5 average rating, 180 reviewsHedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
Sep 7 – 14
Cottage in Smith Island
4.97 out of 5 average rating, 186 reviewsLevering Creek Cottage with Private Docking
Oct 24 – 31
Cottage in Westover
4.99 out of 5 average rating, 182 reviewsRumbley Cottage on the Tangier Sound-Private Beach
Apr 11 – 18
Guest suite in Chincoteague
4.93 out of 5 average rating, 229 reviewsBaywatch North-Waterfront & Roaming Ponies
Dec 2 – 9
Guest suite in Tilghman Island
4.96 out of 5 average rating, 114 reviewsBlack Walnut Cove Retreat, Tilghman Island
Dec 14 – 21
Home in Reedville
4.96 out of 5 average rating, 205 reviewsWaterfront FamilyFriendly Home Improved for 2023
Jan 8 – 15
Farm stay in Cardinal
4.95 out of 5 average rating, 111 reviewsWtrfrnt aptmnt w/pool/dock on private farm
Jun 22 – 29
Chesapeake Bay fishing vacation rentals
Apartment in Stevensville
4.98 out of 5 average rating, 242 reviewsBoutique by the Bay
Mar 15 – 22
Tiny home in Cape Charles
4.98 out of 5 average rating, 275 reviewsThe Laughing King Retreat Honeymoon Island Cottage
Mar 11 – 18
Tiny home in Cambridge
4.89 out of 5 average rating, 500 reviewsBlackwater Tiny Cabin on Snakehead Creek
Aug 21 – 28
Guesthouse in Lusby
4.97 out of 5 average rating, 138 reviewsCozy Lakeside Studio Retreat.
Aug 28 – Sep 4
Guest suite in Piney Point
4.94 out of 5 average rating, 225 reviewsSpectacular beachfront walk-out in Piney Point MD
Dec 31 – Jan 7
Guest suite in Colonial Beach
4.97 out of 5 average rating, 266 reviewsBayview Bungalow
Sep 29 – Oct 6
Guest suite in Arnold
4.96 out of 5 average rating, 569 reviewsOld Bay Bungalow
Jul 27 – Aug 3
Guest suite in Lusby
4.99 out of 5 average rating, 303 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Sep 23 – 30
Chesapeake Bay home rentals
Home in Heathsville
4.93 out of 5 average rating, 122 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
Apr 5 – 12
Home in Lusby
5.0 out of 5 average rating, 112 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
Oct 13 – 20
Home in TYLERTON
4.95 out of 5 average rating, 118 reviews3 bedroom/2.5 bath Smith Island bungalow with dock
Feb 3 – 10
Home in Cambridge
4.92 out of 5 average rating, 182 reviewsGuest House: Farm homestead
Oct 9 – 16
Home in Stevensville
5.0 out of 5 average rating, 102 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Jan 22 – 29
Home in Chestertown
5.0 out of 5 average rating, 156 reviewsNicely refurbished historic house near town center
Mar 14 – 21
Home in Chincoteague Island
4.97 out of 5 average rating, 179 reviews★ Jay’s Waterfront Retreat: Private Dock- Kayaks-Fire Pit-Bikes-Beach-Pet Friendly ★
Jan 19 – 26
Home in Tangier
4.98 out of 5 average rating, 139 reviewsWatermans Hideaway, Tangier Island, Chesapeake Bay
Dec 17 – 24
Destinations to explore
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