Discover Your Perfect Port of Leonardtown Winery Vacation Homes

Best Vacation Homes in Port of Leonardtown Winery

Why Choose Rent By Owner for your Port of Leonardtown Winery 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 Port of Leonardtown Winery

When should you plan your Vacation Rentals stay?

Choosing the right time to visit allows you to fully enjoy the charm of this destination and make the most of your stay in the area’s inviting vacation rentals.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, you can enjoy the region's lush landscapes and blooming vineyards. The weather is warm but comfortable, making it ideal for exploring the scenic surroundings and relaxing at local wineries.

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

This season offers the perfect climate with vibrant fall foliage and harvest festivities. It’s an excellent time for sightseeing and enjoying the region’s wine tastings amid picturesque scenery.

Average Temperature Daytime: 70°F - Nighttime: 50°F

Off-Season Highlights

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Winter (December to February)

Visiting during winter allows you to experience a quieter atmosphere and fewer crowds. The cooler temperatures create a cozy environment, ideal for intimate retreats and enjoying the peaceful countryside.

Average Temperature Daytime: 45°F - Nighttime: 30°F
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Late Fall (November)

As the leaves fall, this time provides a tranquil setting before the holiday rush. It’s a good opportunity for those seeking solitude and a slower pace while exploring the area's scenic vineyards.

Average Temperature Daytime: 55°F - Nighttime: 40°F

Weekly Weather Forecast for Port of Leonardtown Winery

How to Book Your Port of Leonardtown Winery 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 Port of Leonardtown Winery

More Top-Rated Vacation Rentals in Port of Leonardtown Winery 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 outdoor dining spaces perfect for savoring local flavors amidst scenic views.
  • Relish private patios or decks ideal for relaxing and soaking in the fresh air.
  • Make the most of landscaped gardens that provide a peaceful retreat in this area.
  • Take advantage of outdoor grills to host delightful barbecues with family and friends.
  • Experience spacious yards suitable for outdoor games and recreational activities.
  • Utilize designated parking areas for convenience during your stay in this region.
  • Benefit from scenic walking trails or nearby nature spots to explore the natural beauty here.

Top Attractions Around Port of Leonardtown Winery

What attractions are nearby?

Nearby, you can enjoy a variety of outdoor activities and explore charming local attractions that showcase the region’s scenic beauty and vibrant community spirit.

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Family Activities

  • Guided Winery Tours: Discover the region's rich winemaking traditions with family-friendly tours that offer an engaging and educational experience at Port of Leonardtown Winery.
  • Tasting Room Activities for Kids: While adults enjoy local wines, children can participate in interactive tasting activities designed to be fun and informative in this scenic setting.
  • Picnic Areas and Open Spaces: Relax and unwind in the outdoor areas perfect for family picnics, allowing you to soak up the beautiful vineyard views in this tranquil destination.
  • Seasonal Events and Festivals: Join family-friendly events held throughout the year, providing memorable entertainment and engaging activities suitable for all ages in the region.
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Adult Activities

  • Wine Tasting Tours: Experience the region's finest wines through guided tastings at the Port of Leonardtown Winery, a perfect activity to indulge your senses while exploring local vintages.
  • Winery Events and Workshops: Participate in engaging wine-making workshops or special tasting events held regularly at the winery, offering a unique glimpse into the craft of winemaking here.
  • Scenic Vineyard Walks: Enjoy leisurely strolls through the picturesque vineyards surrounding the winery, ideal for relaxing and appreciating the natural beauty of this destination.
  • Photography Opportunities: Capture stunning photos of the scenic landscape and charming winery architecture, making for memorable keepsakes during your visit to the area.

Port of Leonardtown Winery Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local wine tasting tours: Take advantage of the area’s renowned wineries to enjoy authentic Maryland wine experiences during your stay.
  • Plan visits during off-peak hours: To fully appreciate the scenic views and avoid crowds, schedule your winery visits early in the morning or later in the afternoon.
  • Discover nearby dining options: Savor regional cuisine at local eateries close to the winery for a well-rounded visit in this charming region.
  • Book accommodations with scenic views: Choose rental properties that offer picturesque surroundings to enhance your overall experience here in this inviting destination.

Transportation Options

  • Personal Vehicle: Renting or using your own car offers the most flexibility for exploring the area around the winery and enjoying its scenic surroundings.
  • Taxi Services: Local taxi providers provide convenient and reliable transportation options to and from the vineyard, ideal for a comfortable visit here.
  • Rideshare Programs: Rideshare companies operate in the region, offering an easy way to travel without the hassle of parking or navigating unfamiliar roads.
  • Public Transit: Buses serve the area, providing an economical option for visitors looking to explore Port of Leonardtown Winery and nearby attractions with ease.

Local Customs Options

  • Welcoming Hospitality: Locals here pride themselves on their warm, friendly demeanor, making visitors feel at home from the moment they arrive.
  • Celebration of Local Festivals: Participating in traditional festivals and community events is a cherished custom that reflects the area's rich cultural heritage.
  • Respect for Nature and Land: There is a strong emphasis on preserving the natural beauty of the region, often observed through outdoor etiquette and conservation efforts.
  • Emphasis on Maritime Traditions: The local customs often include a reverence for maritime history and practices, which are subtly integrated into daily life and community celebrations.

Frequently Asked Questions About Port of Leonardtown Winery?

1. What are the top vacation rentals in Port of Leonardtown Winery?

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

2. How many Rentbyowner vacation rentals are available in Port of Leonardtown Winery?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 217 in the Port of Leonardtown Winery 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 Port of Leonardtown Winery. 

3. What is the cancellation policy for booking a vacation rental in this area?

The cancellation policy varies depending on the specific property you choose. You should review the individual listing details or contact the property owner directly to understand the applicable terms and any potential fees.

4. How do I secure my reservation at a vacation home in this region?

Reservations are typically secured through the booking platform by following the owner's instructions. Be sure to read the listing carefully for payment requirements and confirmation procedures to ensure a smooth process.

5. Are there any additional fees or charges I should be aware of when booking?

Additional fees such as cleaning, service charges, or taxes may apply and will be outlined in the property listing. Contact the host if you need clarification before finalizing your reservation.

6. What amenities can I expect in the vacation rentals here?

Amenities vary by property, so it’s best to review each listing for specific features. Common amenities include Wi-Fi, fully equipped kitchens, and outdoor spaces, all designed to make your stay comfortable.

7. Is it possible to request special accommodations or flexible check-in times?

Special requests or flexible check-in times depend on the individual property owner. Reach out directly to discuss your needs and confirm availability before confirming your booking.

Best Vacation Homes in Port of Leonardtown Winery

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9.5 (22 Reviews)
Apartment
Retreat at Fenwick
  • Air Conditioner
  • Parking
  • Security/Safety
View Availability
9.0 (14 Reviews)
Bed & Breakfast
Blue Heron Inn - A Bed and Breakfast LLC
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability