Discover Your Perfect Leonardtown Vacation Homes

Leonardtown Luxury Rentals

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Leonardtown Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Leonardtown Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Leonardtown

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit this destination ensures you can enjoy its unique charm and make the most of your stay in the area, whether you're seeking a lively season or a quieter retreat.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, you can enjoy warm weather and longer daylight hours, making it ideal for outdoor activities and exploring the region's scenic beauty.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Early Fall (September to October)

This season offers pleasant temperatures and fewer crowds, providing a perfect setting for relaxing stays and local events in the area.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Winter (December to February)

Visit during the winter months when the region is quieter, offering a peaceful retreat with the chance to enjoy indoor amenities and cozy accommodations.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 40°F
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Late Fall to Early Winter (November to early December)

Experience fewer visitors and cooler temperatures, ideal for those seeking solitude or a more intimate stay in the area’s charming surroundings.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 40°F to 50°F

Weekly Weather Forecast for Leonardtown

How to Book Your Leonardtown Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Leonardtown

More Top-Rated Vacation Rentals in Leonardtown Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor space with a well-maintained backyard or patio area for relaxing and entertaining.
  • Take advantage of outdoor dining options, such as a porch or deck equipped with a grill and seating.
  • Benefit from access to scenic walking trails or nature paths nearby for outdoor exploration.
  • Make the most of outdoor recreational amenities, including a pool or hot tub, available at select properties.
  • Utilize spacious yards for outdoor activities like playing catch, frisbee, or picnicking with family and friends.
  • Relish in beautiful sunset views over the region’s natural landscapes from your outdoor sitting areas.
  • Explore nearby water features, such as docks or access points to lakes or rivers, ideal for kayaking or fishing.

Top Attractions Around Leonardtown

What attractions are nearby?

Within this charming area, you can explore a variety of outdoor activities, cultural attractions, and local events that showcase the best of what makes Leonardtown a unique and inviting destination.

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Family Activities

  • St. Mary's County Museum & Historic District: Explore the region's rich history through engaging exhibits and historic buildings that provide an educational experience for the whole family.
  • Annual Leonardtown Wharf Park Events: Enjoy family-friendly festivals, outdoor concerts, and seasonal celebrations at the scenic wharf area in the center of town.
  • Patuxent River Naval Air Museum: Discover the region’s aviation heritage with interactive displays and aircraft exhibits ideal for curious young minds and history enthusiasts alike.
  • Leonardtown Main Street Shopping and Dining: Stroll along charming streets lined with local shops and cafes, perfect for leisurely family outings and discovering regional crafts and flavors.
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Adult Activities

  • Wine Tasting Tours: Explore local wineries in the region, where you can enjoy tasting sessions and learn about Maryland's wine-making heritage.
  • Historic District Walks: Discover the area's rich history by strolling through charming streets lined with well-preserved landmarks and museums.
  • Take advantage of nearby waterways by renting a boat or kayak for a relaxing day on the water to enjoy scenic views.
  • Art Gallery Visits: Immerse yourself in the regional arts scene by visiting galleries showcasing local artists and unique handcrafted pieces.

Other Places to Stay in Leonardtown, MD

Port of Leonardtown Winery
Port of Leonardtown Winery Vacation Rentals
St. Mary's County
St. Mary's County Vacation Rentals
Compton
Compton Vacation Rentals
More Places to Stay Near Leonardtown

Leonardtown Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Experiences: Take time to enjoy the regional cuisine at local eateries to get a true taste of this destination's culinary heritage.
  • Plan Outdoor Activities: Make the most of the area's scenic parks and waterways by scheduling outdoor adventures that showcase its natural beauty.
  • Visit Seasonal Events: Check out any local festivals or community gatherings happening during your stay to immerse yourself in the area's vibrant culture.
  • Discover Nearby Attractions: Use your vacation rentals as a comfortable base to explore the region’s hidden gems and popular spots alike.

Transportation Options

  • Leonardtown Transit Service: This local bus service offers convenient transportation options within the area, making it easy to explore the region without a car.
  • Taxicab and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available for quick and reliable travel around here.
  • Amtrak Train Station in nearby locations: For longer journeys, you can access Amtrak services from stations in neighboring towns, providing comfortable travel to regional destinations.
  • Car Rentals: Several car rental agencies operate near here, giving you flexible transportation choices during your stay in this destination.

Local Customs Options

  • Rededication to the Arts: Locally, you’ll notice a strong appreciation for arts and crafts, often celebrated through community events and local galleries in Leonardtown.
  • Seafood Cuisine Etiquette: Enjoying fresh seafood is integral here, with casual dining customs emphasizing savoring regional catches like Maryland blue crabs in a friendly setting.
  • Historic Preservation Respect: Respect for the area's historic landmarks is common, as residents take pride in maintaining Leonardtown's rich heritage through conservation efforts.
  • Community Gathering Traditions: Social gatherings frequently involve local festivals and outdoor markets, reflecting the welcoming spirit of this destination’s residents.

Frequently Asked Questions About Leonardtown?

1. What are the top vacation rentals in Leonardtown?

There are a lot of options in Leonardtown. If you plan on staying in the Leonardtown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Leonardtown:

2. How many vacation rentals have private pools in Leonardtown?

There are 5 vacation rentals with private pools near Leonardtown. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Leonardtown are best for families?

If you are looking for a family-friendly vacation home in Leonardtown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Leonardtown:

4. How many Rentbyowner vacation rentals are available in Leonardtown?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 245 in the Leonardtown area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Leonardtown. 

5. What is the cancellation policy for vacation rentals in Leonardtown, Maryland?

Cancellation policies vary depending on the property listing. You should review the specific policy detailed in the rental description or contact the owner directly to understand any fees or restrictions prior to booking.

6. How do I find available vacation rentals with flexible booking options in Leonardtown?

You can filter your search results to display properties offering flexible booking or free cancellation options. It’s recommended to check each listing's details and communicate with the host if you have specific needs for your stay.

7. Are there any house rules I should be aware of when staying in Leonardtown vacation rentals?

Each property will have its own house rules outlined in the listing. Be sure to read these carefully before confirming your reservation, and don’t hesitate to contact the owner if you need clarification.

8. What amenities are typically included with vacation rentals in the region?

Amenities vary by property but often include essentials like Wi-Fi, parking, kitchen facilities, and outdoor spaces. For specific amenities, review the individual listing details or reach out directly to the owner.

9. How do I contact the property owner if I have questions about my stay in Leonardtown?

You can message the owner through the booking platform, which provides a secure way to ask questions or request additional information before finalizing your reservation.

Leonardtown Top Rated Vacation Rentals

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