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 Smith Island
4.97 out of 5 average rating, 186 reviewsLevering Creek Cottage with Private Docking
Dec 4 – 11
Cottage in Leonardtown
4.97 out of 5 average rating, 126 reviewsBeach Front and 'Perfectly Placed'
Sep 26 – Oct 3
Cottage in Onancock
4.97 out of 5 average rating, 198 reviewsEscape to the Eastern Shore - Upscale Waterfront
Nov 24 – Dec 1
Home in Chestertown
4.94 out of 5 average rating, 129 reviewsCHESAPEAKE SUNSETS
Farm stay in Cardinal
4.94 out of 5 average rating, 114 reviewsWtrfrnt aptmnt w/pool/dock on private farm
Aug 5 – 12
Home in Reedville
4.96 out of 5 average rating, 205 reviewsWaterfront FamilyFriendly Home Improved for 2023
Mar 19 – 26
Guest suite in Tilghman Island
4.96 out of 5 average rating, 114 reviewsBlack Walnut Cove Retreat, Tilghman Island
Dec 22 – 29
Cottage in Westover
4.99 out of 5 average rating, 182 reviewsRumbley Cottage on the Tangier Sound-Private Beach
Mar 6 – 13
Chesapeake Bay fishing vacation rentals
Apartment in Stevensville
4.98 out of 5 average rating, 242 reviewsBoutique by the Bay
Feb 13 – 20
Home in Reedville
4.98 out of 5 average rating, 120 reviewsSunkissed Cottage-private, natural waterfront home
Aug 10 – 17
Tiny home in Cambridge
4.89 out of 5 average rating, 500 reviewsBlackwater Tiny Cabin on Snakehead Creek
Jul 31 – Aug 7
Guest suite in Arnold
4.96 out of 5 average rating, 569 reviewsOld Bay Bungalow
Jul 18 – 25
Guest suite in Piney Point
4.94 out of 5 average rating, 225 reviewsSpectacular beachfront walk-out in Piney Point MD
Nov 26 – Dec 3
Cabin in Lusby
4.91 out of 5 average rating, 211 reviewsPeaceful Waterfront Retreat on The Bay
Dec 12 – 19
Guesthouse in Lusby
4.97 out of 5 average rating, 138 reviewsCozy Lakeside Studio Retreat.
Oct 9 – 16
Apartment in Frederica
4.97 out of 5 average rating, 260 reviewsSmokefree Lakeside Relaxation
Oct 14 – 21
Chesapeake Bay home rentals
Home in Heathsville
4.93 out of 5 average rating, 122 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
Jan 12 – 19
Home in TYLERTON
4.95 out of 5 average rating, 118 reviews3 bedroom/2.5 bath Smith Island bungalow with dock
Nov 6 – 13
Home in Lusby
5.0 out of 5 average rating, 112 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
Oct 13 – 20
Home in Gloucester
4.96 out of 5 average rating, 134 reviewsBee Humble Cottage Entire Home
Mar 28 – Apr 4
Home in Cambridge
4.92 out of 5 average rating, 182 reviewsGuest House: Farm homestead
Oct 13 – 20
Home in Stevensville
5.0 out of 5 average rating, 102 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Nov 25 – Dec 2
Home in Chestertown
5.0 out of 5 average rating, 156 reviewsNicely refurbished historic house near town center
Dec 11 – 18
Home in Tangier
4.98 out of 5 average rating, 139 reviewsWatermans Hideaway, Tangier Island, Chesapeake Bay
Jan 6 – 13
Destinations to explore
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