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
Chesapeake Bay waterfront vacation rentals
Tiny home in Saint Inigoes
4.98 out of 5 average rating, 301 reviewsHistoric St.Mary's City at the Lazy Bear Cottage
Home in Cape Charles
4.99 out of 5 average rating, 105 reviewsModern Private Beach House close to Cape Charles
Cottage in Heathsville
4.94 out of 5 average rating, 184 reviewsHedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
Tiny home in Accomac
4.93 out of 5 average rating, 446 reviewsLittle Red House on a Farm - Quiet Rural Waterview
Guesthouse in Yorktown
4.97 out of 5 average rating, 211 reviewsCharming Yorktown Battlefield Cottage
Cottage in Saint Michaels
4.98 out of 5 average rating, 142 reviewsLa Casita on Harris Creek, St. Michaels
Apartment in North
4.97 out of 5 average rating, 197 reviewsLittle Cove Cottage, Couples Retreat/Mathews
Home in Reedville
4.98 out of 5 average rating, 125 reviewsSunkissed Cottage-private, natural waterfront home
Chesapeake Bay fishing vacation rentals
Guest suite in Piney Point
4.94 out of 5 average rating, 230 reviewsSpectacular beachfront walk-out in Piney Point MD
Tiny home in Cambridge
4.88 out of 5 average rating, 510 reviewsBlackwater Tiny Cabin on Snakehead Creek
Guest suite in Colonial Beach
4.97 out of 5 average rating, 275 reviewsBayview Bungalow
Guest suite in Lusby
4.99 out of 5 average rating, 310 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Guesthouse in Saluda
4.93 out of 5 average rating, 479 reviewsWooded Cabin retreat on fresh water pond
Loft in Cape May Court House
4.97 out of 5 average rating, 594 reviewsQuiet Lakefront Studio - Close to the Beach
Guesthouse in Riva
4.99 out of 5 average rating, 278 reviewsThe Riva House
Guest suite in Arnold
4.96 out of 5 average rating, 577 reviewsOld Bay Bungalow
Chesapeake Bay house rentals
Home in Reedville
4.96 out of 5 average rating, 209 reviewsWaterfront FamilyFriendly Home Improved for 2023
Home in Heathsville
4.94 out of 5 average rating, 129 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
Home in Gloucester
4.96 out of 5 average rating, 137 reviewsBee Humble Cottage Entire Home
Home in Cambridge
4.93 out of 5 average rating, 187 reviewsGuest House: Farm homestead
Home in Virginia Beach
4.9 out of 5 average rating, 214 reviewsQuilted Quarters by the Bay with Private Entrance
Home in TYLERTON
4.95 out of 5 average rating, 120 reviews3 bedroom/2.5 bath Smith Island bungalow with dock
Home in Lusby
4.98 out of 5 average rating, 266 reviewsCove Point Beach Cabin
Home in Charles City
4.99 out of 5 average rating, 236 reviewsHutch's Bluff - Waterfront near Williamsburg
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