Vacation rentals in Kennedyville

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Top-rated vacation rentals in Kennedyville

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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

SUPERHOST

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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