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Vacation rentals in Kennedyville

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Top-rated vacation rentals in Kennedyville

Guests agree: these stays are highly rated for location, cleanliness, and more.

Cottage in Kennedyville
NEW! Family-Friendly Cottage, Walk to the Beach!
Make your days as enjoyable as possible with this versatile and child-proofed vacation rental! Fully equipped with kayaks, bikes, a popcorn machine, gas stove, Nespresso machine, milk frother, and more, this 2-bedroom, 1-bath dwelling is within walking distance to a branch of the Chesapeake Bay for even more relaxation gratification — there’s even a playground to entertain your kiddos! Visit nearby marinas, wineries, and breweries for a complete tour of Kennedyville, Chestertown, and Rock Hall.
$181 per night
Rental unit in Chestertown
Secluded Cottage in Middle of Chestertown
Escape to a secluded, romantic studio getaway in the middle of Chestertown. Private parking, and over an acre of gardens to call your own. Enjoy the fire with views of nature all around, this is the perfect place to relax. Kitchenette has extra large toaster oven, (can cook pizza and roast chicken), 2 burner hot plate, microwave, refrigerator, and coffee maker. Comfortable queen bed, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a large house in front of the carriage house.
$120 per night
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Cabin in Goldsboro
Wigwam Lodge *MasterSuite & Lounge* Woodland Views
Wigwam Lodge is an experience nestled in a pine & hard wood forest with rural privacy. Incredibly spacious decks. Surround Forest Views inside and out! 5-min from Choptank river, 20-min from Historic Denton, Irish Pub & Grocery, 1hr from the beach. Easy PARKING 10ft from the front door Click “Show More” Below to SEE ALL Deets
$125 per night
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Other great vacation rentals in Kennedyville

Home in Chestertown
Merry Manor Pet Friendly Home
$125 per night
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Home in Kennedyville
Comfy and Cozy on the Eastern Shore
$135 per night
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Home in Chestertown
Cozy 3-bedroom home w/ screened in porch & firepit
$165 per night
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Cabin in Abingdon
The Fox Cabin - Perfect to Relax
$79 per night
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Guesthouse in Chestertown
Cozy Carriage House
$101 per night
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Private room in Still Pond
Master BD ( Room 1 ) in Civil War House
$101 per night
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Home in Kennedyville
Perfect for Hunters on the Eastern Shore
$150 per night
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Serviced apartment in Betterton
Victorian by the Bay Suite
$210 per night
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Rental unit in Chestertown
1-br apt in downtown Chestertown
$150 per night
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Serviced apartment in Chestertown
Hillside Waterfront historic district 1BR Apt.
$150 per night
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Home in Chestertown
Simple Living on the Pond
$103 per night
Home in Chestertown
CHESAPEAKE SUNSETS
$138 per night
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