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
Cottage in Onancock
4.97 out of 5 average rating, 198 reviewsEscape to the Eastern Shore - Upscale Waterfront
Nov 24 – Dec 1
Cottage in Saint Leonard
4.99 out of 5 average rating, 102 reviewsCaptain Jack's Bay Hideaway
May 30 – Jun 6
Home in Reedville
4.96 out of 5 average rating, 204 reviewsWaterfront FamilyFriendly Home Improved for 2023
Mar 24 – 31
Home in Heathsville
4.93 out of 5 average rating, 122 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
Feb 16 – 23
Cottage in Leonardtown
4.97 out of 5 average rating, 126 reviewsBeach Front and 'Perfectly Placed'
Jan 24 – 31
Tiny home in Accomac
4.93 out of 5 average rating, 441 reviewsLittle Red House on a Farm - Quiet Rural Waterview
Mar 23 – 30
Cottage in Westover
4.99 out of 5 average rating, 182 reviewsRumbley Cottage on the Tangier Sound-Private Beach
Feb 24 – Mar 3
Cottage in Smith Island
4.97 out of 5 average rating, 185 reviewsLevering Creek Cottage with Private Docking
Feb 20 – 27
Chesapeake Bay fishing vacation rentals
Apartment in Stevensville
4.98 out of 5 average rating, 240 reviewsBoutique by the Bay
Feb 7 – 14
Tiny home in Cape Charles
4.98 out of 5 average rating, 275 reviewsThe Laughing King Retreat Honeymoon Island Cottage
Mar 28 – Apr 4
Tiny home in Cambridge
4.89 out of 5 average rating, 498 reviewsBlackwater Tiny Cabin on Snakehead Creek
Jul 29 – Aug 5
Cottage in Heathsville
4.94 out of 5 average rating, 180 reviewsHedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
Aug 7 – 14
Guest suite in Piney Point
4.94 out of 5 average rating, 225 reviewsSpectacular beachfront walk-out in Piney Point MD
Mar 27 – Apr 3
Guest suite in Lusby
4.99 out of 5 average rating, 303 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Apr 24 – May 1
Loft in Cape May Court House
4.97 out of 5 average rating, 591 reviewsQuiet Lakefront Studio - Close to the Beach
Nov 10 – 17
Guest suite in Tilghman Island
4.96 out of 5 average rating, 114 reviewsBlack Walnut Cove Retreat, Tilghman Island
Aug 5 – 12
Chesapeake Bay home rentals
Home in TYLERTON
4.95 out of 5 average rating, 118 reviews3 bedroom/2.5 bath Smith Island bungalow with dock
Aug 9 – 16
Home in Lusby
5.0 out of 5 average rating, 111 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
Oct 16 – 23
Home in Lusby
4.98 out of 5 average rating, 261 reviewsCove Point Beach Cabin
Sep 22 – 29
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Dec 25 – Jan 1
Home in Gloucester
4.95 out of 5 average rating, 133 reviewsBee Humble Cottage Entire Home
Mar 23 – 30
Home in Chestertown
5.0 out of 5 average rating, 155 reviewsNicely refurbished historic house near town center
Jan 18 – 25
Home in Crisfield
4.95 out of 5 average rating, 254 reviewsCozy Home near Waterfront in Crisfield, MD
Jan 26 – Feb 2
Home in Virginia Beach
4.9 out of 5 average rating, 207 reviewsQuilted Quarters by the Bay with Private Entrance
Nov 30 – Dec 7
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