Discover Your Perfect Port of Leonardtown Winery Rentals by Owner

Port of Leonardtown Winery Rentals by Owner

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9.5 (22 Reviews)
Apartment
Retreat at Fenwick
  • Air Conditioner
  • Parking
  • Security/Safety
View Availability
More Top-Rated Rentals by Owner in Port of Leonardtown Winery Area

Why Choose Rent By Owner for your Port of Leonardtown Winery vacation rental?

What makes our Rentals by Owner 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 Rentals by Owner stay?

To make the most of your visit, consider planning your vacation during the area's peak seasons or quieter times to enjoy a more relaxed experience at this destination in Leonardtown, Maryland.

Peak Season Highlights

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Spring (March to May)

During spring, this area comes alive with vibrant landscapes, making it an ideal time to visit the winery for a serene experience amidst blooming gardens.

Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
autumn
Fall (September to November)

Autumn offers picturesque views and harvest festivities, perfect for enjoying wine tastings and exploring the region's scenic beauty.

Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F

Off-Season Highlights

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Winter (December to February)

The quiet winter months provide a peaceful retreat with fewer visitors, allowing you to savor the tranquility of this destination.

Average Temperature Daytime: 40-50°F - Nighttime: 25-35°F
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Summer (June to August)

While summer is popular, the peak heat can be intense; visiting during early or late summer allows for more comfortable exploration of the area.

Average Temperature Daytime: 80-90°F - Nighttime: 60-70°F

Weekly Weather Forecast for Port of Leonardtown Winery

How to Book Your Port of Leonardtown Winery vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Rentals by Owner in Port of Leonardtown Winery Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 seating areas perfect for relaxing amidst scenic views in this region.
  • Take advantage of private gardens or landscaped yards ideal for outdoor gatherings.
  • Make use of designated barbecue grills for preparing meals outdoors during your stay.
  • Utilize spacious decks or patios to enjoy the fresh air and charming surroundings.
  • Benefit from access to outdoor dining spaces to savor meals al fresco.
  • Explore well-maintained walking paths or trails directly accessible from your rental.
  • Relax in outdoor lounge furniture designed for comfort while taking in the local scenery.

Top Attractions Around Port of Leonardtown Winery

What attractions are nearby?

Nearby, you can enjoy a variety of activities that highlight the charm of the region, making your stay in this destination both relaxing and memorable.

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Family Activities

  • Wine Tasting and Vineyard Tours: Experience family-friendly wine tastings and guided vineyard tours that showcase the region's renowned craftsmanship.
  • Picnic at the Winery Grounds: Enjoy a relaxing picnic with your loved ones amidst scenic views and lush landscapes, perfect for unwinding in this charming area.
  • Educational Winery Workshops: Participate in interactive workshops designed to introduce children and adults alike to the art of winemaking and viticulture.
  • Scenic Walking Trails: Take leisurely strolls along picturesque trails surrounding the winery, offering stunning views and opportunities for family photos in the region.
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Adult Activities

  • Wine Tasting Experiences: Indulge in guided tastings of locally crafted wines that showcase the region's rich viticultural heritage.
  • Join a Winery Tour: Explore the scenic vineyard grounds and learn about the winemaking process from knowledgeable staff here in the area.
  • Participate in Wine and Food Pairing Events: Enhance your visit with curated pairings that highlight regional flavors, perfect for adult enthusiasts.
  • Attend Special Events and Festivals: Experience seasonal celebrations and live entertainment hosted at the winery, offering an authentic taste of local culture.

Port of Leonardtown Winery Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Wineries: Take advantage of the region's renowned wineries to enjoy tastings and tours that deepen your appreciation for the area's viticulture.
  • Visit Nearby Attractions: Use your stay as a base to explore nearby historical sites and scenic spots that showcase the charm of this destination.
  • Plan Outdoor Activities: Maximize your visit by engaging in outdoor pursuits such as boating, fishing, or walking along scenic trails in the vicinity.
  • Support Local Dining: Dine at local eateries to experience authentic regional cuisine and connect more intimately with the community here.

Transportation Options

  • Personal Vehicles: Renting or driving your own car provides the most flexibility when exploring this scenic region, allowing you to visit nearby attractions comfortably.
  • Taxi Services: Local taxi services offer convenient point-to-point transportation around the area, making short trips effortless during your stay.
  • Rideshare Options: Rideshare companies operate here, providing a reliable and cost-effective way to travel without the need for personal transportation.
  • Bicycle Rentals: Biking is an eco-friendly alternative that lets you enjoy the area's natural beauty while getting around at your own pace.

Local Customs Options

  • Greeting Etiquette: When visiting local establishments, you’ll find that a warm handshake or friendly nod is customary to show respect in the area.
  • Conversation Topics: Engaging in conversations about regional history or local events is appreciated and often encourages a more meaningful connection with residents here.
  • Dining Customs: Tipping around 15-20% at restaurants reflects good etiquette, which aligns with the friendly hospitality typical of this region.
  • Festive Traditions: Participating in seasonal festivals or community gatherings offers an authentic way to experience the area’s unique customs and local pride.

Frequently Asked Questions About Port of Leonardtown Winery Rentals by Owner

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 150 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 a rental by owner in Port of Leonardtown Winery?

Cancellation policies vary depending on the individual property listing. It’s recommended to review the specific cancellation terms outlined on the listing or contact the owner directly to understand your options.

4. How do I know if my booking at a rental in this area is secure?

Bookings made through Rent By Owner are protected by trusted secure payment systems, and reviews from previous guests can help ensure a reliable and trustworthy stay with the owner.

5. Are there any specific check-in or check-out requirements I should be aware of?

Check-in and check-out details are typically provided by the owner upon confirmation of your reservation. Be sure to review these specifics on the listing or communicate directly with the owner for any special instructions.

6. Can I modify or cancel my reservation once booked?

Modifications and cancellations depend on the policies set by the owner. It’s important to read the individual listing details thoroughly or reach out to the owner to confirm the process and any potential fees.

7. What amenities are usually included in rentals by owner in this region?

Amenities vary between properties, but many rentals offer essential comforts such as Wi-Fi, kitchen facilities, and parking. Check each listing’s description for a detailed list of what’s included before booking.

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More Top-Rated Rentals by Owner in Port of Leonardtown Winery Area