1. USA
  2. Maryland
  3. Smith Island
  4. Tylerton
  5. Rentals by Owner

Discover Your Perfect Tylerton Rentals by Owner

Tylerton Rentals by Owner

More Top-Rated Rentals by Owner in Tylerton Area

Why Choose Rent By Owner for your Tylerton vacation rental?

What makes our Rentals by Owner special?

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

Best Times to Visit Tylerton

When should you plan your Rentals by Owner stay?

Choosing the optimal time to visit here ensures you enjoy the region's best weather and local events, making your rental by owner experience in Tylerton, Smith Island, Maryland, USA, truly memorable.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, you'll enjoy warm weather and longer daylight hours, making it ideal for exploring the scenic surroundings of the island.

Average Temperature Daytime: 75-85°F - Nighttime: 60-70°F
autumn
Early Fall (September to October)

This season offers pleasant temperatures and less crowded conditions, perfect for experiencing the tranquil beauty of the area while booking your vacation rental.

Average Temperature Daytime: 70-80°F - Nighttime: 55-65°F

Off-Season Highlights

image
Winter (December to February)

The quiet winter months provide a peaceful retreat with cooler temperatures, offering a different, serene experience when staying in rentals here.

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

At this time, fewer visitors are around, allowing you to enjoy the area's natural beauty in a more exclusive setting while finding great rental deals.

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

Weekly Weather Forecast for Tylerton

How to Book Your Tylerton 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 Tylerton

More Top-Rated Rentals by Owner in Tylerton 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 dining spaces with scenic views of the surrounding water and natural landscape.
  • Take advantage of private decks or patios ideal for relaxing or entertaining outdoors.
  • Make use of communal or private boat docks for easy access to local waterways and fishing activities.
  • Benefit from outdoor grilling areas to prepare fresh seafood and regional cuisine.
  • Relax in a hammock or lounge chair while soaking up the tranquil ambiance of the area.
  • Explore landscaped gardens or spacious yards that enhance your outdoor experience.
  • Utilize designated outdoor recreational areas perfect for hiking, birdwatching, or enjoying the region’s natural beauty.

Top Attractions Around Tylerton

What attractions are nearby?

During your stay, you'll have the opportunity to explore a variety of nearby activities that showcase the natural beauty and outdoor charm of the region, making your visit both memorable and enriching.

image
image

Family Activities

  • Smith Island Cultural Center Tour: Discover the rich history and local traditions of the region through engaging exhibits and hands-on experiences in this educational center.
  • Bird Watching on the Island: Enjoy observing diverse bird species in their natural habitat, making it a perfect outdoor activity for families seeking nature encounters.
  • Exploring the Island’s Beaches: Relax and play along the pristine shores, where you can build sandcastles, collect shells, or simply enjoy the serene ocean views.
  • Kayaking Adventures: Paddle through calm waters around the area, offering an exciting way to explore the waterways and see local marine life up close.
image

Adult Activities

  • Bird Watching Tours: Discover the region's rich avian diversity by exploring local bird watching spots that cater to enthusiasts seeking a peaceful nature experience.
  • Kayaking Adventures: Enjoy tranquil paddle trips along the waters surrounding this destination, offering an immersive way to view the scenic coastline and wildlife.
  • Maritime Museum Visits: Delve into the area's maritime history through engaging exhibits and educational programs that highlight the island's seafaring heritage.
  • Local Seafood Dining: Savor fresh seafood at nearby eateries renowned for showcasing the region’s culinary traditions rooted in coastal flavors.

Other Places to Stay in Tylerton, MD

Smith Island
Explore 47 Properties
More Places to Stay Near Tylerton

Tylerton Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Arrival Carefully: Schedule your trip during a time when transportation options to this island destination are most reliable to ensure a smooth start to your stay.
  • Embrace Local Hospitality: Take advantage of the warm, inviting atmosphere by engaging with hosts who can provide insider tips for experiencing the region's hidden gems.
  • Utilize the Natural Setting: Make the most of the scenic surroundings by exploring outdoor activities that highlight the area's unique coastal environment.
  • Respect the Community and Environment: Practice eco-friendly habits and honor local customs to help preserve the tranquility and beauty of this island getaway.

Transportation Options

  • Boat Transportation: You can easily reach your rental on this island via private or scheduled boat services, offering a scenic and direct way to access the area.
  • Charter Services: Personalized boat charters are available for exploring the surrounding waters, providing a flexible option to travel to and from the region.
  • Ferry Connections: Regular ferry routes connect nearby mainland locations with the island, ensuring smooth and reliable transportation for visitors staying here.
  • Private Water Taxis: For quick and convenient transfers, water taxis operate frequently, giving you a comfortable means of getting around while enjoying the coastal views.

Local Customs Options

  • Traditional Fishing Practices: Locals here have a long-standing tradition of sustainable fishing, which is integral to the area's cultural identity.
  • Seafood Celebrations: Celebrating fresh seafood through community events highlights the region’s rich maritime heritage and local customs.
  • Island Hospitality: Visitors often experience warm, welcoming interactions reflecting the genuine hospitality typical of this destination’s residents.
  • Preservation of Local Crafts: Artisans in the area keep traditional crafts alive, offering unique handmade items that embody the region’s cultural essence.

Frequently Asked Questions About Tylerton Rentals by Owner

1. What are the top vacation rentals in Tylerton?

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

2. How many Rentbyowner vacation rentals are available in Tylerton?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 30 in the Tylerton 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 Tylerton. 

3. What is the cancellation policy for rental properties in Tylerton, Smith Island?

The cancellation policies vary depending on the individual owner and listing. You should review the specific cancellation terms outlined in the property listing or contact the owner directly for detailed information.

4. How do I communicate with the property owner before booking?

You can reach out to the owner through the messaging system provided on Rent By Owner. It's recommended to ask any questions about the property, availability, or special requests prior to completing your reservation.

5. Are there any additional fees for rentals in this area?

Additional fees such as cleaning, service charges, or security deposits are specified in the listing details. Review these carefully on the property page or contact the owner if you have questions about extra costs.

6. Is it possible to get a flexible check-in or check-out time?

Check-in and check-out times are determined by the owner and should be confirmed in the listing. If you have specific timing needs, contact the owner directly to discuss potential arrangements.

7. What amenities are typically included in rentals owned here?

Rentals by owner in this destination often include essential amenities such as Wi-Fi, kitchen facilities, and linens. For a complete list of amenities, see the property description or contact the owner for clarification.

More Rentals You May Like Near Tylerton

8.8 (55 Reviews)
House
Paradise Awaits.
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
8.8 (46 Reviews)
House
Cottage near the Bay
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
More Top-Rated Rentals by Owner in Tylerton Area