Discover a selection of 65 vacation rentals in Leonardtown, MD that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $100 per night, and houses and cottages are popular options for a stay in Leonardtown. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Leonardtown
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, Vrbo 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.

How many vacation rentals are available around Leonardtown, MD?

Our 2021 property listings offer a large selection of 65 vacation rentals around Leonardtown. From 60 house rentals to 12 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Leonardtown?

Yes, of course. Vrbo has 60 Houses in Leonardtown. Our other popular types of vacation rentals in Leonardtown include:

  • Cottages: 12 rentals available
  • Condos/Apartments: 3 rentals available
  • Cabins: 12 rentals available

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

Can I find a vacation rental with pool in Leonardtown?

Yes, you can select your preferred vacation rental with pool among our 11 vacation rentals with pool available in Leonardtown. Please use our search bar to access the selection of vacation rentals available.