Photo by Pla Jira

Leonardtown holiday lettings

We found 62 holiday rentals — enter your dates for availability

Discover a selection of 11 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.

Holiday rentals with weekly discounts - Leonardtown

Showing deals for:14 Nov - 21 Nov

Image gallery for Unplug and unwind at your Leonardtown waterfront vacation home!

Miscellaneous
9.2 out of 10 rating
Wonderful
(7 reviews)

Unplug and unwind at your Leonardtown waterfront vacation home!

Leonardtown, MD

7% off
Price is £1,912
£273 per night
includes taxes & fees
Unplug and unwind at your Leonardtown waterfront vacation home!

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, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Leonardtown

Find out more about Leonardtown

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:

  • Port of Leonardtown Winery (1.4 mi / 2.3 km)
  • Maryland International Raceway (13 mi / 21 km)
  • Hague Winery (15.1 mi / 24.3 km)
  • Running Hare Vineyard (15.1 mi / 24.3 km)
  • Perigeaux Vineyards and Winery (11.2 mi / 18.1 km)
  • Wicomico Shores Golf Course (13.3 mi / 21.3 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)
  • Annmarie Sculpture Garden and Arts Center (10.5 mi / 16.9 km)
  • Piney Point Beach (12.2 mi / 19.6 km)
  • Battle Creek Cypress Swamp Sanctuary (14 mi / 22.6 km)
  • Matoaka Beach (15 mi / 24.2 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 an excellent choice. This charming area is steeped in history and offers a delightful atmosphere for visitors. One of the highlights of the historic district is the Leonardtown Wharf Park, which provides scenic views of the water and is great for leisurely walks or picnics. Additionally, the nearby St. Mary's County Historical Society offers fascinating insights into the region's past, making it an ideal spot for history enthusiasts.

Another appealing option is the area around the Leonardtown Town Centre. This vibrant neighbourhood is known for its array of shops, restaurants, and local events. Staying here allows easy access to the Leonardtown Arts and Entertainment District, where you can enjoy local galleries and live performances. The blend of modern amenities and quaint charm makes it a popular choice for holiday rentals, with numerous properties available to suit various preferences and budgets.
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, Maryland, travellers should consider the scenic waterfront areas along the Patuxent River. The neighbourhoods near the Leonardtown Wharf offer a picturesque setting, with properties that often feature private decks, outdoor seating, and easy access to the riverfront. Many rentals in this area come equipped with modern amenities, including fully furnished kitchens and spacious living areas, making them ideal for families or groups looking to enjoy a relaxing getaway by the water.

Additionally, the nearby Breton Bay area is known for its charming beach homes and cottages, which provide a more secluded atmosphere. Here, visitors can find properties that often include private beach access, outdoor grills, and amenities such as kayaks or paddleboards for water activities. The proximity to local parks and nature trails adds to the appeal, allowing guests to explore the natural beauty of the region.
What is the most popular type of holiday rental accomodation in Leonardtown?
In Leonardtown, holiday houses are the most popular choice, with around 10 available in the area. These properties typically feature spacious layouts, multiple bedrooms, and amenities such as fully equipped kitchens and outdoor spaces superb for relaxation. Many are located in charming neighbourhoods close to local attractions like the Leonardtown Wharf and historic sites. Additionally, there are several apartments and cottages available, which provide a more compact but equally comfortable alternative for travellers.
Are there any family house rentals in Leonardtown?
In Leonardtown, Maryland, there are several family-friendly house rentals available, great for those looking to enjoy a getaway in this charming area. Properties in the vicinity often feature spacious living rooms, fully equipped kitchens ideal for preparing family meals, and outdoor patios or gardens where children can play and families can relax.
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, making it an excellent choice for travellers looking to explore this charming area with their furry companions. Many of these rentals are equipped with modern amenities such as fully stocked kitchens, outdoor spaces, and comfortable living areas, ensuring a pleasant stay.
Are there any remote work holiday rentals in Leonardtown?
In Leonardtown, Maryland, there are several remote work holiday rentals available, with around 13 options to choose from. This charming town, known for its quaint streets and rich history, offers properties that cater to the needs of remote workers. Many of these rentals come equipped with essential amenities such as Wi-Fi, dedicated workspaces with desks, and comfortable desk chairs, ensuring a productive environment during your stay. 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, holiday rentals typically offer a range of convenient amenities that cater to travellers' needs. Common features include kitchens equipped with microwaves, refrigerators, and toasters, allowing guests to prepare their own meals. Additionally, cookware, dishware, and utensils are often provided, enhancing the home-like feel of the accommodations.
When is the best time to visit Leonardtown for a holiday rental?
The best time to visit Leonardtown for a holiday rental is during the vibrant peak season from May to July, with July being the most popular month. This period is superb for those seeking a delightful blend of outdoor activities and cultural experiences. With warm temperatures averaging in the mid to high 20s Celsius, visitors can comfortably explore the charming streets, enjoy waterfront activities, and participate in local events, including the infamous Leonardtown annual festivities that celebrate the town's rich heritage.

May marks the beginning of the peak season, offering a lovely spring atmosphere with blooming flowers and ideal conditions for outdoor sightseeing. The pleasant climate is superb for leisurely strolls along the waterfront or picnics in the nearby parks, allowing you to soak in the stunning natural beauty of the area.

If you're looking for a more budget-friendly option, consider visiting Leonardtown in December. While it's the low season, this month brings its own charm with festive decorations and local holiday events that create a warm and inclusive setting. You can enjoy the quieter streets and take part in seasonal festivities without the hustle and bustle of peak tourist crowds.
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.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

More Holiday Rentals ideas

Olney Holiday Rentals
Standard Link for Olney
Lusby Holiday Rentals
Standard Link for Lusby
Davenport Holiday Rentals
Standard Link for Davenport
Gambrills Holiday Rentals
Standard Link for Gambrills
Adamstown Holiday Rentals
Standard Link for Adamstown
North East Holiday Rentals
Standard Link for North East
Salisbury Holiday Rentals
Standard Link for Salisbury
Sarasota Holiday Rentals
Standard Link for Sarasota
San Diego Holiday Rentals
Standard Link for San Diego
Taylors Island Holiday Rentals
Standard Link for Taylors Island
Stowe Holiday Rentals
Standard Link for Stowe
Naples Holiday Rentals
Standard Link for Naples
Annapolis Holiday Rentals
Standard Link for Annapolis
Chesapeake Beach Holiday Rentals
Standard Link for Chesapeake Beach
Destin Holiday Rentals
Standard Link for Destin
Berlin Holiday Rentals
Standard Link for Berlin
Severna Park Holiday Rentals
Standard Link for Severna Park
Gaithersburg Holiday Rentals
Standard Link for Gaithersburg
Friendsville Holiday Rentals
Standard Link for Friendsville
Palm Springs Holiday Rentals
Standard Link for Palm Springs
McHenry Holiday Rentals
Standard Link for McHenry
Rockville Holiday Rentals
Standard Link for Rockville
Tilghman Holiday Rentals
Standard Link for Tilghman
Ocean City Holiday Rentals
Standard Link for Ocean City
St. Michaels Holiday Rentals
Standard Link for St. Michaels
Key West Holiday Rentals
Standard Link for Key West
Hagerstown Holiday Rentals
Standard Link for Hagerstown

People also search for

Naples Villas
Standard Link for Naples
Rockville Apartments
Standard Link for Rockville
Gatlinburg Cabin Rentals
Standard Link for Gatlinburg