Discover Your Perfect Tilmon's Island Winery Rentals by Owner

Tilmon's Island Winery Rentals by Owner

10.0 (89 Reviews)
Apartment
Eastern Shore Get Away
  • Air Conditioner
  • Parking
  • TV
View Availability
More Top-Rated Rentals by Owner in Tilmon's Island Winery Area

Why Choose Rent By Owner for your Tilmon's Island 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 Tilmon's Island Winery

When should you plan your Rentals by Owner stay?

Timing your visit to this charming area can enhance your experience, so consider planning your vacation during the local seasons that showcase the region's natural beauty and tranquility to make the most of your stay.

Peak Season Highlights

spring
Spring (March to May)

During the spring months, you can enjoy the region's lush landscapes and blooming vineyards, making it an ideal time for vineyard tours and outdoor activities.

Average Temperature Daytime: 60°F to 75°F - Nighttime: 45°F to 55°F
autumn
Fall (September to November)

Autumn is a popular time here for wine tasting experiences amid the vibrant fall foliage, attracting visitors seeking scenic beauty and harvest festivities.

Average Temperature Daytime: 65°F to 70°F - Nighttime: 50°F to 55°F

Off-Season Highlights

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Winter (December to February)

Visit during the winter months to enjoy quieter surroundings and cozy winery visits, though outdoor activities are limited due to colder weather.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 40°F
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Summer (June to August)

Though summer offers warm weather, this period tends to be less crowded, providing a more relaxed experience for your stay here.

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

Weekly Weather Forecast for Tilmon's Island Winery

How to Book Your Tilmon's Island 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 Tilmon's Island Winery

More Top-Rated Rentals by Owner in Tilmon's Island 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 and taking in the scenic views of the region.
  • Make the most of well-maintained gardens or landscaped yards that enhance your outdoor stay.
  • Take advantage of private patios or decks to unwind in the fresh air during your visit.
  • Use outdoor grills or barbecue equipment provided for memorable cookouts with family and friends.
  • Benefit from access to expansive lawns or open spaces ideal for outdoor activities and games.
  • Explore nearby trails or pathways that allow you to experience the natural beauty of this area firsthand.
  • Relax in outdoor fire pits or fireplaces, creating cozy moments under the stars during your vacation.

Top Attractions Around Tilmon's Island Winery

What attractions are nearby?

Discover a variety of outdoor activities and scenic attractions just moments from the winery, offering you a perfect opportunity to explore the natural beauty and local charm of this region while enjoying your stay through Rent By Owner.

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Family Activities

  • Wine Tasting Tours: You can enjoy guided wine tasting experiences tailored for families on the scenic grounds of the winery, perfect for discovering local flavors in a relaxed setting.
  • Outdoor Picnic Areas: Bring your family and unwind at the picturesque picnic spots on site, where you can savor a meal amidst beautiful vineyard views.
  • Vineyard Tours: Embark on a family-friendly tour through the lush vineyards to learn about the winemaking process in this charming region.
  • Special Family Events: Participate in seasonal festivals and events hosted here that offer engaging activities suitable for children and adults alike.
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Adult Activities

  • Wine Tasting Tours: Enjoy guided tastings at the winery, where you can sample a variety of expertly crafted wines unique to the region.
  • Vineyard Walks: Stroll through the scenic vineyards surrounding the area, experiencing the beauty and tranquility of this popular destination.
  • Winery Events: Attend special events such as wine release parties or seasonal celebrations that highlight local traditions and flavors.
  • Educational Workshops: Participate in winemaking classes or tasting seminars designed to deepen your understanding of regional viticulture.

Tilmon's Island Winery Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During Off-Peak Hours: To enjoy a more relaxed experience at the winery and avoid crowds, consider scheduling your visit during weekdays or early in the day.
  • Explore Local Dining Options: Take advantage of nearby eateries to complement your stay, allowing you to savor regional flavors that enhance your visit here.
  • Book Your Accommodation Well in Advance: Secure your rental by owner early to ensure availability and to secure the best options for your preferred dates in this area.
  • Engage with the Winery Staff: Interact with the knowledgeable staff to gain insights about the region’s wine heritage and hidden gems for a truly authentic experience.

Transportation Options

  • Personal Vehicle: Renting or bringing your own car provides the most flexibility for exploring the surrounding area of Tilmon's Island Winery and enjoying local sights at your own pace.
  • Local Taxi Services: Taxis are readily available in the region, offering convenient transportation options for short trips within Sudlersville and nearby attractions.
  • Ride-Sharing Apps: Popular ride-sharing services operate here, providing a reliable and easy way to get around without the need for personal transportation.
  • Public Transportation: Bus services connect the area with larger cities and regional hubs, making it easier to access the winery and other local destinations without a car.

Local Customs Options

  • Greetings and Personal Space: It is customary here to greet others with a friendly nod or wave, and respecting personal space is appreciated during social interactions in this charming region.
  • Cheese and Local Food Sharing: Sharing local delicacies, especially regional cheeses and fresh produce, is a valued tradition when visiting the area, fostering a sense of community among guests and locals alike.
  • Respect for the Land and Nature: Visitors often observe a deep respect for the natural surroundings, including avoiding littering and adhering to designated paths when exploring this destination’s scenic vineyard and countryside.
  • Celebratory Toasts and Hospitality: Raising a glass to toast special moments is common in social gatherings in the region, highlighting the warm hospitality that welcomes visitors to enjoy the area's rich wine culture.

Frequently Asked Questions About Tilmon's Island Winery Rentals by Owner

1. What are the top vacation rentals in Tilmon's Island Winery?

There are a lot of options in Tilmon's Island Winery. If you plan on staying in the Tilmon's Island 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 Tilmon's Island Winery:

2. How many Rentbyowner vacation rentals are available in Tilmon's Island Winery?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 61 in the Tilmon's Island 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 Tilmon's Island Winery. 

3. What is the cancellation policy for rentals by owner in this region?

The cancellation policy varies depending on the specific rental listing. You should review the terms outlined in the listing details or contact the owner directly to understand the applicable cancellation conditions.

4. How do I confirm my booking with a rental owner in this area?

Bookings are confirmed once you complete the reservation process through Rent By Owner and receive a confirmation from the property owner. Be sure to review all details and communicate any questions before confirmation.

5. Are there any additional fees I should be aware of when booking a rental in this destination?

Additional fees, such as cleaning fees or service charges, may apply and will be detailed in the listing. Always read the full fee breakdown before finalizing your reservation.

6. What amenities are typically included in rentals by owner here?

Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, and parking. For specific amenities, refer to the individual listing or reach out to the owner for clarification.

7. How can I contact the property owner if I have questions about my stay?

You can contact the owner directly through the messaging system on Rent By Owner. It’s recommended to clarify any queries before completing your reservation to ensure a smooth stay.

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More Top-Rated Rentals by Owner in Tilmon's Island Winery Area