Leonardtown holiday rentals

We found 63 holiday rentals — enter your dates for availability

Discover a selection of 12 homes and other holiday rentals in Leonardtown that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the amenities that you need and want for your stay, which might include parking and a washer and dryer. What you'll find is a property to rent for everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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 accommodation options with space to entertain friends and family, HomeAway 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 searching for things to do during your stay? Venture out of your holiday home and check out everything that makes Leonardtown a one-of-a-kind holiday spot. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Breton Bay Golf Course (2.3 mi / 3.7 km)
  • 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)
  • Wicomico Shores Golf Course (13.3 mi / 21.3 km)
  • Michael P. O'Brien Athletics and Recreation Center (13.4 mi / 21.6 km)

Exploring the natural features in Leonardtown

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Leonardtown is a great place to get outside. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • St. Mary's River State Park (5.1 mi / 8.2 km)
  • St. Clement's Island State Park (8 mi / 12.9 km)
  • Piney Point Beach (12.2 mi / 19.6 km)
  • Battle Creek Cypress Swamp Sanctuary (14 mi / 22.6 km)
  • Flag Ponds Nature Park (14.4 mi / 23.2 km)
  • Saint George Island Beach (14.6 mi / 23.6 km)

How to get to and around Leonardtown

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

Frequently asked questions

How much does it cost to rent a holiday home in Leonardtown?
Season, property type and length of stay are some things that can influence the price of a holiday home. Simply click on your travel dates to find your perfect match. From cosy chalets to expansive villas, all Stayz holiday homes 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 travelling. All you have to do is enter your travel dates into Stayz and the number of guests to see your home 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 holiday home in Leonardtown?
The minimum age is generally 16, 18 or 21. It can differ across properties on Stayz, so look at the rules of your chosen Leonardtown holiday home before you book.
How long can I rent a holiday home in Leonardtown for?
How long you can rent a holiday home 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.