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
Cottage in Onancock
4.97 out of 5 average rating, 201 reviewsEscape to the Eastern Shore - Upscale w dock
Home in Reedville
4.98 out of 5 average rating, 122 reviewsSunkissed Cottage-private, natural waterfront home
Guest suite in Piney Point
4.94 out of 5 average rating, 227 reviewsSpectacular beachfront walk-out in Piney Point MD
Tiny home in Cape Charles
4.98 out of 5 average rating, 276 reviewsThe Laughing King Retreat Honeymoon Island Cottage
Farm stay in Cardinal
4.91 out of 5 average rating, 117 reviewsWtrfrnt aptmnt w/pool/dock on private farm
Cottage in Leonardtown
4.96 out of 5 average rating, 130 reviewsBeach Front and 'Perfectly Placed'
Home in Heathsville
4.94 out of 5 average rating, 124 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
Cottage in Smith Island
4.97 out of 5 average rating, 189 reviewsLevering Creek Cottage with Private Docking
Chesapeake Bay fishing vacation rentals
Apartment in Stevensville
4.98 out of 5 average rating, 242 reviewsBoutique by the Bay
Guest suite in Colonial Beach
4.97 out of 5 average rating, 269 reviewsBayview Bungalow
Guesthouse in Church Road
5.0 out of 5 average rating, 138 reviewsHeron Rock: Lakefront Cottage on Lake Chesdin
Tiny home in Cambridge
4.89 out of 5 average rating, 506 reviewsBlackwater Tiny Cabin on Snakehead Creek
Apartment in Frederica
4.97 out of 5 average rating, 262 reviewsSmokefree Lakeside Relaxation
Cottage in Gloucester Courthouse
4.98 out of 5 average rating, 196 reviewsHistoric Ware River Cottage at Glebefield
Tiny home in Deltaville
4.98 out of 5 average rating, 114 reviewsVirginia Dare
Cabin in Lusby
4.94 out of 5 average rating, 150 reviewsHideaway on the Bay: Waterfront Vintage A Frame
Chesapeake Bay home rentals
Home in Reedville
4.96 out of 5 average rating, 206 reviewsWaterfront FamilyFriendly Home Improved for 2023
Home in Charles City
4.99 out of 5 average rating, 234 reviewsHutch's Bluff - Waterfront near Williamsburg
Home in Gloucester
4.96 out of 5 average rating, 136 reviewsBee Humble Cottage Entire Home
Home in Shady Side
5.0 out of 5 average rating, 121 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Home in Chestertown
5.0 out of 5 average rating, 157 reviewsNicely refurbished historic house near town center
Home in Stevensville
5.0 out of 5 average rating, 103 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Home in Annapolis
4.96 out of 5 average rating, 116 reviewsHistoric Downtown in-law suite
Home in Milton
4.99 out of 5 average rating, 191 reviewsON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.
Destinations to explore
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