31 Properties in Leonardtown, Maryland, United States of America. June 7, 2026 through June 8, 2026

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St. Mary's River State Park

New Towne Neck State Park

Port of Leonardtown Winery

Sandyland Beach

Leonard's Grant Community Area

Saint Mary's Fairground

The Shoppes at McIntosh

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Leonardtown

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31 properties

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Two Adirondack chairs facing a pier extending into a body of water.

A room with a wooden bench, a small table, and a view of the outdoors.

Rustic 3BR Waterfront Cabin with Firepit + Dock Access

Entire home by Vrbo

Sleeps 7 · 3 bedrooms · 1.5 bathrooms

1010 out of 10

Exceptionalexceptional

1 review(1 review)

$505 nightly

The current price is $802 total

$802 total

Total with taxes and fees

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A large, two-story house with a wrap-around porch and multiple windows.

A wooden double door with glass panels, a porch with a railing, and a view of the outdoors.

Swanendele Inn at St. Mary's Maryland

Breakfast included

9.89.8 out of 10

Exceptionalexceptional

34 reviews(34 reviews)

$625 nightly

The current price is $694 total

$694 total

Total with taxes and fees

We have 1 left at this price

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2 Bedroom Cottage at Coles Point Marina

Entire home by Vrbo

Sleeps 6 · 2 bedrooms · 2 bathrooms

Washer and dryer

$345 nightly

The current price is $423 total

$423 total

Total with taxes and fees

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Photo gallery for Rustic 3BR Waterfront Cabin with Firepit + Dock Access

Rustic 3BR Waterfront Cabin with Firepit + Dock Access

Photo gallery for Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland

Photo gallery for 2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina