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    Check prices for these dates, 15 – 16 December 2026

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    Our top choices for Kennedyville holiday rentals

    1. Peaceful Farmhouse Getaway on a Working Farm

    A modern kitchen with stainless steel appliances, a central island, and bar stools.

    2. First Floor Studio Apartment in Historic Chestertown

    A house with a swimming pool, surrounded by a fence, and two red umbrellas.

    3. Newly restored apartment in the heart of Chestertown

    A spacious living area with a dining table, sofa, and a kitchen in the background.

    4. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

    A wooden staircase leading to a beach with a clear view of the sea.

    5. Turtle Cove Room

    A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

    6. Beachcomber Suite

    A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

    7. Guest Suite for up to 2 in a Victorian on the Chester River

    A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

    8. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

    A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

    9. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

    A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

    10. Historic Chesapeake City Stay

    A riverside dock with boats, a covered seating area, and a bridge in the background.

    11. BAYSIDE BUNGALOW

    A building with a gabled roof and a circular vent on the roof.

    12. Long Beach Cottage, (romantic couple’s getaway)

    A room with a large sliding glass door leading to a balcony with a view of the sea and a wooden deck.

    13. Bohemia Manor Farm

    Restaurant

    14. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

    A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

    15. Waterfront house with amazing views. Top of the Chesapeake

    A wooden deck with lounge chairs and a dock extending into calm water.

    16. Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

    A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

    17. Country Get Away Studio Apartment

    A wooden cabin with a porch, surrounded by dense forest.

    18. Bohemia Hideaway. Escape to a 14 acre peaceful retreat.

    A modern living room with a flat-screen TV, a brown sofa, a dining table with placemats, wicker chairs, and a kitchen area with a microwave and stove.

    19. 5-bedroom vacation home 5 minutes from historic Charlestown

    A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

    20. Charming 2-bedroom house in Aberdeen with WiFi and AC

    A living room with teal walls, a black sofa, a patterned rug, a flat-screen TV on a wooden stand, and a painting on the wall.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Top Kennedyville Hotel Reviews

    Hampton Inn & Suites Edgewood/Aberdeen-South

    A modern hotel lobby with a long dining table, several chairs, and a bar area.

    Holiday Inn Express & Suites Middletown by IHG

    A lobby area with seating, a reception desk, and a refrigerator stocked with beverages.

    Vandiver Inn

    A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.

    Red Roof Inn & Suites Chestertown

    A living room with a fireplace, a television, and a stone accent wall.

    City Express by Marriott Aberdeen

    A hotel entrance with a clear sign reading "LA QUINTA".

    Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

    A buffet area with multiple self-service stations, including trays of omelets and other prepared foods.

    Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

    A spacious living area with a staircase, a fireplace, a sofa, and a dining area.

    Hampton Inn & Suites Baltimore/Aberdeen

    A spacious hotel lobby with a large seating area, a television, a fireplace, and a coffee station.

    Hampton Inn Middletown

    An indoor swimming pool with clear blue water, a tiled deck, and a view of the outside building.

    Find out more about Kennedyville

    Everything you need to know about Kennedyville holiday rentals

    Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kennedyville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

    There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kennedyville holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Kennedyville holiday rentals: An excellent choice for every season

    Whenever you want to travel, a warm welcome awaits you in Kennedyville. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

    Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kennedyville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Kennedyville holiday rentals we have selected for you start as low as £76 per night. Entering your travel dates in the search wizard you might find even better deals!

    How to find incredible deals on Kennedyville rentals

    At Expedia, we put the best Kennedyville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

    To find some top Kennedyville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kennedyville holiday.

    If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kennedyville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

    Frequently Asked Questions

    Can I find a holiday rental in Kennedyville?

    Yes, there are holiday rentals close to the most popular sights in Kennedyville, or you can select a more secluded option if you're looking for a relaxing stay.

    What are some of the best holiday rentals that Kennedyville has to offer?

    Sailor's Sunrise Cottage - Chesapeake Bay: This holiday home rental outside of Kennedyville is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

    What’s there to see and do in Kennedyville?

    Turner Creek Landing Park and Turner's Creek Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Crow Farm and Vineyard and Kent Museum.

    What’s a holiday rental in Kennedyville like?

    Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kennedyville. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family trips or small group gatherings.