Leonardtown Holiday Homes from €217: Search Top House Rentals

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Leonardtown holiday homes

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

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

Leonardtown

Carol L.

includes taxes & fees

1 Dec - 2 Dec

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

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

California

includes taxes & fees

17 Nov - 18 Nov

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

3. 4-BR Waterfront Turret Home

Solomons

Thomas S.

includes taxes & fees

17 Nov - 18 Nov

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

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

Montross

Julie P.

includes taxes & fees

15 Nov - 16 Nov

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

5. Charming Waterfront 3-bedroom house in Piney Point

Piney Point

Meira

includes taxes & fees

14 Nov - 15 Nov

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

6. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

includes taxes & fees

13 Nov - 14 Nov

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

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

Lexington Park

Andrea B.

includes taxes & fees

16 Nov - 17 Nov

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

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

Lusby

Dani B.

includes taxes & fees

18 Nov - 19 Nov

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

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

Lusby

includes taxes & fees

16 Nov - 17 Nov

A backyard with a fire pit surrounded by green Adirondack chairs, a wooden fence, and a house with string lights.

10. 7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

Colonial Beach

Crystal W.

includes taxes & fees

16 Nov - 17 Nov

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

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

Montross

Nicole P.

includes taxes & fees

1 Dec - 2 Dec

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

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

Lusby

Alexander B.

includes taxes & fees

13 Nov - 14 Nov

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

13. Bright and airy waterfront getaway

Benedict

George

includes taxes & fees

13 Nov - 14 Nov

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.

14. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lusby

Tanya S.

includes taxes & fees

15 Nov - 16 Nov

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

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

Montross

N C.

includes taxes & fees

15 Nov - 16 Nov

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

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

Prince Frederick

Sean B.

includes taxes & fees

20 Nov - 21 Nov

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

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

King George

Kelley M.

includes taxes & fees

15 Nov - 16 Nov

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

18. Covenant Cove - Cove Point Beach

Lusby

includes taxes & fees

19 Nov - 20 Nov

A wooden gazebo with benches, a yellow-painted floor, and a view of the ocean.

19. Available for Winter Festival/Firepit/Grill/One Level

Colonial Beach

Cynthia H.

includes taxes & fees

15 Nov - 16 Nov

View all properties

Find holiday rentals that suit your style

Cottages

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Leonardtown Hotel Reviews

River Edge Inn

10/10 Excellent

"Everything was great! Thank you so much"

Find out more about Leonardtown

Leonardtown Holiday Homes information

Number of reviews	265
Accommodation	271 Holiday Homes
Lowest Price	€217
Highest Price	€976

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Leonardtown holiday homes

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