Leonardtown holiday lettings

We found 62 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.

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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 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)
  • Wicomico Shores Golf Course (13.3 mi / 21.3 km)
  • Michael P. O'Brien Athletics and Recreation Center (13.4 mi / 21.6 km)
  • Running Hare Vineyard (15.1 mi / 24.3 km)
  • Hague Winery (15.1 mi / 24.3 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)
  • Cedar Cove Community Beach Recreation Area (12.9 mi / 20.8 km)
  • Battle Creek Cypress Swamp Sanctuary (14 mi / 22.6 km)
  • Flag Ponds Nature Park (14.4 mi / 23.2 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

What is the best area to stay in Leonardtown when booking a holiday rental?
When considering a holiday rental in Leonardtown, Maryland, the historic district is the best area to stay. This charming neighbourhood is known for its picturesque streets and well-preserved architecture, which provide a delightful glimpse into the area's rich history. Staying here allows easy access to top attractions such as the St. Mary's County Historical Society Museum, where you can learn about the local heritage, and the scenic Leonardtown Wharf, superb for a leisurely stroll along the water.

In the historic district, you'll find a variety of properties, ranging from quaint cottages to modern rentals, suiting different tastes and budgets. The sense of community and the vibrant setting, especially during local events and festivals, make this area particularly appealing for visitors looking to immerse themselves in the local culture.
How much does it cost to rent a holiday home in Leonardtown?
Prices for holiday rentals in Leonardtown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Leonardtown to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Leonardtown holiday house rentals?
You can find great discounts on house rentals in Leonardtown on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Leonardtown?
For renting a beach house in Leonardtown, travellers should consider the picturesque areas along the Patuxent River and the nearby Chesapeake Bay. The region boasts lovely waterfront homes that offer stunning views and easy access to serene beaches. Properties in and around Leonardtown typically come with amenities such as private docks, outdoor decks, and spacious gardens, ideal for families or groups looking to enjoy the outdoors.

The nearby St. Mary's County offers a variety of rental options near popular spots like Point Lookout State Park, where visitors can find houses equipped with modern kitchens, barbeque grills, and fire pits for evening gatherings. These rentals often provide a great blend of relaxation and adventure, with opportunities for fishing, kayaking, and beachcombing right at your doorstep.

Moreover, Leonardtown itself is rich in history and charm, featuring quaint shops and restaurants that add to the overall experience. Many beach houses in this area also highlight local attractions, making it easy for guests to explore the nearby historical sites and natural beauty while enjoying comfortable accommodations.
What is the most popular type of holiday rental accomodation in Leonardtown?
In Leonardtown, holiday houses are the most popular type of holiday rental, with about 33 available in the area. These properties typically offer spacious rooms, featuring multiple bedrooms, fully equipped kitchens, and outdoor areas ideal for relaxing after a day of exploring. Additionally, there are several apartments and cottages that provide a cozier alternative, often located in charming neighbourhoods close to local attractions such as the Leonardtown Wharf and historical sites.
Are there any family house rentals in Leonardtown?
In Leonardtown, Maryland, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The town boasts charming properties that often feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can play and explore. Many of these homes also provide amenities like Wi-Fi and air conditioning to ensure a comfortable stay.

The neighbourhood is close to various attractions, including the picturesque Leonardtown Wharf, where families can enjoy scenic walks and picnics by the water. Additionally, nearby points of interest like St. Mary's County Museum and the historic downtown area offer opportunities for cultural enrichment and local dining experiences.
Can I find long-stay holiday rentals in Leonardtown?
A long-stay holiday rental in Leonardtown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Leonardtown?
In Leonardtown, there are several pet-friendly house rentals available for travellers looking to enjoy a getaway with their furry companions. Many of these properties come equipped with amenities such as spacious backyards, outdoor seating areas, and fully equipped kitchens, providing comfort and convenience for families or groups.

The town itself offers a charming atmosphere with local shops and eateries that may welcome pets, ideal for pet owners. Additionally, nearby points of interest, like the scenic Leonardtown Wharf Park, provide lovely walking paths along the water, making it an ideal spot for leisurely strolls with your dog.
Are there any remote work holiday rentals in Leonardtown?
In Leonardtown, Maryland, there are numerous options for remote work holiday rentals, with around 42 properties available. This quaint town, known for its charming historic district and waterfront views, offers a variety of accommodations suitable for those looking to work remotely. Many of these rentals come equipped with essential amenities such as high-speed internet and Wi-Fi, ensuring you can stay connected during your stay. Additionally, you'll often find spaces with dedicated work areas, including desks and comfortable chairs, superb for setting up a home office environment.

Leonardtown also provides a delightful backdrop for downtime, with local attractions such as the St. Mary's County Museum and the scenic waterfront along Breton Bay. After work, you can explore the nearby parks or enjoy dining at local eateries that showcase the region's seafood and Southern Maryland cuisine. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Leonardtown holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Leonardtown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Leonardtown?
In Leonardtown, popular rental amenities include kitchens, which allow guests to prepare their own meals, and decks or patios for enjoying the pleasant outdoor surroundings. Many properties also feature onsite parking, making it convenient for visitors travelling by car. Additionally, porches or lanais provide a welcoming space to relax and take in the views. A coffee or tea maker is typically available in rentals, ensuring that guests can enjoy a warm beverage at their leisure.
When is the best time to visit Leonardtown for a holiday rental?
The peak season for visiting Leonardtown is from May to July, with July being the most popular month for holiday rentals. This vibrant period draws in travellers eager to explore the charming town and its picturesque surroundings, making the most of the warm summer weather. Expect temperatures to hover around 25 to 30 degrees Celsius, making it ideal for outdoor activities like strolling along the waterfront, visiting local parks, or enjoying outdoor dining.

During this time, visitors can experience firsthand the local culture, with numerous events and festivals showcasing the best of Leonardtown's community spirit. The lively option is superb for families and groups seeking memorable experiences together.

For those looking for a more budget-friendly option, consider visiting in December. While this is the low season, Leonardtown transforms into a picturesque winter wonderland, offering a peaceful retreat. You can enjoy the festive decorations, explore the quaint shops, and partake in seasonal events, all while avoiding the crowds.

Ultimately, the best time to book a holiday rental in Leonardtown depends on whether you prefer the bustling energy of the summer months or the serene charm of winter.
How early should I book a Leonardtown holiday rental?
Book your Leonardtown holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Leonardtown?
In Leonardtown, visitors can experience firsthand a blend of history and natural beauty. The heart of the town features the Historic Leonardtown Square, where charming boutiques, art galleries, and restaurants create a vibrant setting. Here, you can also find the St. Mary's County Historical Society, which offers insights into the local heritage.

For those interested in the outdoors, the nearby Leonardtown Wharf Park provides scenic views of the Patuxent River, along with walking trails and picnic areas, making it a lovely spot for relaxation. The park often hosts community events and concerts, adding to the local culture.

Art enthusiasts will appreciate the nearby Annmarie Sculpture Garden & Arts Centre, which showcases a variety of outdoor sculptures and offers art exhibitions. The peaceful setting is superb for a leisurely stroll while enjoying the artistic creations.

Additionally, Leonardtown serves as a gateway to the waters of the Chesapeake Bay, with opportunities for boating, fishing, and exploring the nearby islands.
Can I change or cancel my Leonardtown home rental booking on Vrbo?
To find Leonardtown holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Leonardtown holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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