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A rural landscape with a barn, trees, and a fence under a sunset sky.

Leonardtown Vacation Rentals

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    Check prices for these dates, December 15–16, 2026

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    Our top choices for Leonardtown vacation homes

    1. 2 Acre Oasis with Private Beach! Family and dog friendly!

    A modern kitchen with granite countertops, stainless steel appliances, and large windows offering views of the outdoors.

    2. 8BD Retreat | Hot Tub, Movie Room, Gym & Pool

    A bedroom with a bed, a ceiling fan, two windows with curtains, a bedside lamp, a potted plant, and a door.

    3. 4-BR Waterfront Turret Home

    A spacious living room with a large sofa, a television, and a view of the ocean.

    4. Waterfront Retreat w/Private Hot Tub · Game Room · Fire Pit · Kayaks

    A coastal area with a sandy beach, a clear blue sea, and a small settlement with houses.

    5. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

    A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

    6. Solomons Spacious 6-BD Family Home with Hot Tub

    A backyard with a wooden bench, two white cushioned chairs, a table, and a tree providing shade.

    7. 7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

    A bedroom with a bed, a nightstand, a window with curtains, and a view of the outside.

    8. Charming Waterfront 3-bedroom house in Piney Point

    A two-story house with a balcony, surrounded by trees and a wooden fence.

    9. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

    A covered patio with a view of a lake, furnished with chairs and a table.

    10. Waterfront Reset: Views, Games, Boats & Total Calm

    An outdoor patio with a glass table and chairs, a blue umbrella, and a view of a lake.

    11. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

    A pathway lined with trees and lights leading to a wooden building with a visible window.

    12. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

    A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

    13. Bright and airy waterfront getaway

    A lakeside view with chairs and a table, a rainbow, and trees.

    14. Riverfront Home w/Dock · Fire Pit · Kids Play Area

    A modern kitchen with grey cabinets, a large island with bar stools, and a view of the living area.

    15. Lakefront Cabin Near Solomons Island w/ Hot Tub

    A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

    16. Lusby 3BD Family Beach House - Steps to the Sand!

    A room with a wooden floor, a gray sofa, a blue armchair, and a table.

    17. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

    A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

    18. Cozy 3 Bdrm home in King George. 5 mins to Dahlgren Naval Base and Southern MD

    A small, single-story house with a red door, a porch with white railings, and a brick pathway leading to the entrance.

    19. Covenant Cove - Cove Point Beach

    A covered patio area with a table and chairs, large windows, and a ceiling fan.

    20. River Refresh - Waterfront with Spa on Placid Bay

    A deck with outdoor furniture overlooking a lake.

    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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    Learn more about Leonardtown

    Explore the historic waterfront square where local artisans showcase their crafts and restaurants serve fresh Chesapeake Bay seafood. Kayak along Breton Bay's peaceful waters or visit the nearby Patuxent River Naval Air Museum in Lexington Park.

    See all hotels in Leonardtown

    A rural landscape with a barn, trees, and a fence under a sunset sky.

    Top reviews in Leonardtown

    Spark by Hilton California Lexington Park

    A multi-story hotel with a covered entrance and a parking lot.

    Hampton Inn by Hilton Lexington Park

    A hotel lobby with a dining area, seating, a fireplace, and a view of the outside through large windows.

    Island Inn & Suites, an Ascend Collection Hotel

    A hotel room with a large bed, a nightstand with a lamp, a wooden wardrobe, and a window with blinds.

    La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

    A modern hotel lobby with seating areas, a reception desk, and a staircase.

    Hilton Garden Inn Solomons

    A covered outdoor seating area with wicker furniture and large windows.

    My Place Hotel - Dahlgren/King George, VA

    Private kitchen

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