Destination guide

The picturesque setting of Leonardtown is ready to explore

Enjoy the festivals and other features of Leonardtown. This city's seafood restaurants, sporting events and kayaking draw many visitors. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.


Activities and attractions in Leonardtown

Are you searching for things to do while you're in the area? Venture out of your cozy vacation rental and experience everything that makes Leonardtown a fun place to get away. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Hague Winery (12.8 mi / 20.6 km)
  • Perigeaux Vineyards and Winery (12.9 mi / 20.8 km)
  • Maryland International Raceway (14.7 mi / 23.7 km)
  • General's Ridge Vineyard and Winery (15.9 mi / 25.5 km)
  • Vault Field Vineyards (16.8 mi / 27 km)
  • Running Hare Vineyard (17.4 mi / 28 km)
Natural features

Exploring the natural landscape of Leonardtown

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Leonardtown is a great place to get outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city center:

  • St. Mary's River State Park (4.3 mi / 6.9 km)
  • St. Clement's Island State Park (7 mi / 11.3 km)
  • Greenwell State Park (9.6 mi / 15.5 km)
  • Annmarie Sculpture Garden and Arts Center (11.3 mi / 18.1 km)
  • Jefferson Patterson Park and Museum (11.7 mi / 18.9 km)
  • Elms Beach Park (14.9 mi / 24 km)
How to get there

Transportation options to and around Leonardtown

The nearest airport is in Washington, DC (DCA-Ronald Reagan Washington National), located 46.5 mi (74.9 km) from the city center.

Where to stay around Leonardtown?

Our 2019 property listings offer a large selection of 49 vacation rentals near Leonardtown. From 35 Houses to 10 Cabins, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Leonardtown for a holiday or a weekend are on HomeAway.

What are the popular points of interest near where I can stay when traveling to Leonardtown?

HomeAway offers a large selection of vacation rentals near lovely places in Leonardtown. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Cove Point Lighthouse: 99 vacation rentals
  • Breezy Point Beach: 186 vacation rentals
  • Westmoreland State Park: 84 vacation rentals
  • Point Lookout State Park: 97 vacation rentals
  • Patuxent River Naval Air Station: 101 vacation rentals

But there are many other points of interest around Leonardtown listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Leonardtown?

Yes, of course. HomeAway has 35 Houses in Leonardtown. Our other popular types of vacation rentals in Leonardtown include:

  • Cabins: 10 rentals available
  • Cottages: 10 rentals available
  • Bungalows: 10 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Country houses and more.

Can I find a vacation rental with pool in Leonardtown?

Yes, you can select your preferred vacation rental with pool among our 9 vacation rentals with pool available in Leonardtown. Please use our search bar to access the selection of vacation rentals available.

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