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Leonardtown vacation rentals

We found 51 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 10 homes and other vacation rentals in Leonardtown that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the amenities you expect for your stay, such as WiFi and cable TV. You'll be able to choose a rental to meet everyone's needs, including options that are accessible or non-smoking.

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    Enjoy full kitchens, laundry, pools, yards and more
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  • A place for everyone
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The picturesque setting of Leonardtown is ready to explore

Enjoy the festivals and other features of Leonardtown. Renowned for its seafood restaurants, sporting events and kayaking, this city welcomes all visitors. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Leonardtown

Are you hoping to find top things to see and do in the city? Venture out of your cozy vacation rental and check out everything that makes Leonardtown a fun spot to vacation. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Maryland International Raceway (13 mi / 21 km)
  • Running Hare Vineyard (15.1 mi / 24.3 km)
  • Port of Leonardtown Winery (1.4 mi / 2.3 km)
  • Perigeaux Vineyards and Winery (11.2 mi / 18.1 km)
  • Hague Winery (15.1 mi / 24.3 km)
  • R&J's PlayPark (16.9 mi / 27.2 km)

Exploring the natural features in Leonardtown

Whether you're looking for fun outdoor activities or just want to take in the scenery, Leonardtown is a great place to spend some time outside. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Calvert Cliffs State Park (13 mi / 20.9 km)
  • Westmoreland State Park (16 mi / 25.7 km)
  • Colonial Beach (17.8 mi / 28.7 km)
  • Point Lookout State Park (23.8 mi / 38.3 km)
  • St. Mary's River State Park (5.1 mi / 8.2 km)
  • Jefferson Patterson Park and Museum (10.3 mi / 16.6 km)

How to get to and around Leonardtown

Fly into Ronald Reagan Washington National Airport (DCA), the closest airport, located 44.3 mi (71.4 km) from the city center.

Frequently asked questions

How much does it cost to rent a vacation rental in Leonardtown?

Season, property type and length of stay are some things that can influence the price of a vacation home. Simply click on your travel dates to find your perfect match. From cozy chalets to expansive villas, all Vrbo vacation rentals offer terrific value.

How much does it cost to rent a beach house in Leonardtown?

Prices for beach houses in Leonardtown will vary depending on the type and size of the property and time of year you're traveling. All you have to do is enter your travel dates into Vrbo and the number of guests to see your rental options and prices. From there you can use our filters to tailor your search by amenities, nearby activities, ratings and more.

What are the top attractions for families in Leonardtown?

Keep your kids entertained at these fabulous family-friendly attractions in Leonardtown:

  • St. Marys River State Park
  • St. Clements Island State Park
  • Greenwell State Park

How old do you have to be to rent a vacation rental in Leonardtown?

The minimum age is generally 16, 18 or 21. It can differ across properties on Vrbo, so look at the rules of your chosen Leonardtown vacation rental before you book.

How long can I rent a vacation rental in Leonardtown for?

How long you can rent a vacation rental in Leonardtown is up to the property. Simply enter your desired travel dates to display a list of options offering extended stays. With lots of amenities such as kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to find somewhere just right to call your home away from home in Leonardtown.

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