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
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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
Cottage in Westover
4.99 out of 5 average rating, 183 reviewsRumbley Cottage on the Tangier Sound-Private Beach
Cottage in Smith Island
4.97 out of 5 average rating, 187 reviewsLevering Creek Cottage with Private Docking
Cottage in Leonardtown
4.97 out of 5 average rating, 126 reviewsBeach Front and 'Perfectly Placed'
Guest suite in Piney Point
4.94 out of 5 average rating, 225 reviewsSpectacular beachfront walk-out in Piney Point MD
Farm stay in Cardinal
4.94 out of 5 average rating, 114 reviewsWtrfrnt aptmnt w/pool/dock on private farm
Home in Heathsville
4.93 out of 5 average rating, 122 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
Home in Reedville
4.96 out of 5 average rating, 205 reviewsWaterfront FamilyFriendly Home Improved for 2023
Chesapeake Bay fishing vacation rentals
Apartment in Stevensville
4.98 out of 5 average rating, 242 reviewsBoutique by the Bay
Tiny home in Cambridge
4.89 out of 5 average rating, 500 reviewsBlackwater Tiny Cabin on Snakehead Creek
Tiny home in Cape Charles
4.98 out of 5 average rating, 275 reviewsThe Laughing King Retreat Honeymoon Island Cottage
Cabin in Lusby
4.91 out of 5 average rating, 211 reviewsPeaceful Waterfront Retreat on The Bay
Guesthouse in Lusby
4.97 out of 5 average rating, 138 reviewsCozy Lakeside Studio Retreat.
Guest suite in Arnold
4.96 out of 5 average rating, 570 reviewsOld Bay Bungalow
Guest suite in Lusby
4.99 out of 5 average rating, 305 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Guest suite in Colonial Beach
4.97 out of 5 average rating, 266 reviewsBayview Bungalow
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
Home in Lusby
5.0 out of 5 average rating, 112 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
Home in Gloucester
4.96 out of 5 average rating, 134 reviewsBee Humble Cottage Entire Home
Home in Stevensville
5.0 out of 5 average rating, 102 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Home in Chestertown
5.0 out of 5 average rating, 156 reviewsNicely refurbished historic house near town center
Home in Cambridge
4.92 out of 5 average rating, 182 reviewsGuest House: Farm homestead
Home in Tangier
4.98 out of 5 average rating, 139 reviewsWatermans Hideaway, Tangier Island, Chesapeake Bay
Home in Woolford
4.93 out of 5 average rating, 118 reviewsWaterfront Getaway with Dock
Destinations to explore
- Yurt Rentals United States
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- Castle Rentals United States
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- Farm Cottages United Kingdom
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