Leonardtown holiday lettings
Find the best place to stay - Leonardtown
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Find spaces that suit your style
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, pools, gardens and more
- More for lessMore 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:
- 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 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:
- 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 National Airport (DCA), the closest airport, located 44.3 mi (71.4 km) from the city centre.