Discover Your Ideal Smith Island vacation rentals in Tylerton for a memorable Maryland escape
Discover Your Perfect Tylerton Vacation Homes
Best Vacation Homes in Tylerton
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Tylerton Luxury Rentals
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Tylerton Pet Friendly Vacation Rentals
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Tylerton Large Vacation Homes
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Why Choose Rent By Owner for your Tylerton Vacation Rental Homes?
What makes our Vacation Rentals special?
Best Times to Visit Tylerton
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit can enhance your experience here, as seasonal trends in this region influence everything from weather to local activities, making it essential to plan your stay accordingly for a memorable getaway.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, you'll experience warm weather ideal for enjoying the scenic views and outdoor activities in the area.
Late Summer to Early Fall (August to September)
This time offers the warmest temperatures and is perfect for soaking up the local atmosphere while avoiding the peak crowds.
Off-Season Highlights
Early Spring (March to April)
Visit during this quieter season when the region begins to awaken from winter, providing a more tranquil atmosphere for your stay.
Late Fall to Early Winter (October to November)
Experience a peaceful retreat as the area transitions into cooler months, with fewer visitors and serene surroundings.
Weekly Weather Forecast for Tylerton
How to Book Your Tylerton Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Tylerton
Common Vacation Rentals Amenities
What amenities can you expect?
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 where you can relax and take in scenic views of the surrounding waters.
- Benefit from private decks or porches that provide a perfect spot for morning coffee or evening unwinding.
- Make use of on-site picnic areas, ideal for outdoor dining amid the tranquil atmosphere.
- Take advantage of outdoor grills available for preparing delicious meals during your stay.
- Utilize well-maintained walking paths or trails that allow you to explore the natural beauty of this destination.
- Relish in access to fishing spots directly from the property, offering a peaceful outdoor experience.
- Seek outdoor recreational equipment such as kayaks or paddleboards, often provided for guest enjoyment in this regional haven.
Top Attractions Around Tylerton
What attractions are nearby?
In this charming destination, you can enjoy exploring natural wildlife habitats, observing local bird species, and engaging in tranquil waterside activities just moments from your stay.

Family Activities
- Clamming and Crabbing: Engage in a fun and educational activity by trying your hand at clamming or crabbing in the shallow waters surrounding this island destination.
- Exploring the Maritime Museum: Discover local maritime history and enjoy interactive exhibits that captivate both children and adults alike, offering an enriching experience here.
- Wildlife Watching: Observe diverse bird species and other wildlife in their natural habitats, making it a perfect outdoor adventure for nature-loving families visiting the area.
- Kayaking Adventures: Rent kayaks and paddle through serene waters, providing a tranquil way to explore the scenic coastline and nearby marshlands together.
Adult Activities
- Birdwatching Tours: Experience the diverse bird species unique to this island region, making it a peaceful and enriching activity for nature enthusiasts.
- Historical Site Visits: Explore the local history through visits to preserved sites that offer insight into the area's cultural heritage.
- Seafood Dining Experiences: Indulge in fresh, locally caught seafood at waterfront restaurants that showcase the region’s culinary traditions.
- Boating and Fishing Excursions: Enjoy guided boat trips or fishing adventures that let you immerse yourself in the scenic waterways surrounding the island.
Other Places to Stay in Tylerton, MD
Tylerton Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Transportation: Arrange transportation options in advance to explore the area comfortably, as private or public transit on this destination can be limited.
- Embrace the Natural Beauty: Take time to enjoy the scenic views and outdoor activities that highlight the region’s unique coastal environment.
- Respect Local Customs and Environment: Be mindful of the island’s community and natural surroundings to ensure a sustainable and enjoyable visit.
- Choose Your Accommodation Wisely: Select a well-reviewed vacation rental that offers convenient access to key spots around the region for a more immersive experience.
Transportation Options
- Ferry Services: You can opt for ferry rides that connect the island to the mainland, offering scenic views and a reliable way to travel to this peaceful destination.
- Private Boat Rentals: Renting a private boat allows you to explore the surrounding waters at your own pace, providing both convenience and a unique experience here.
- Charter Cruises: Charter cruises offer personalized transportation options with expert guides, perfect for sightseeing and making the most of your visit to this region.
- Water Taxis: Water taxis operate frequently between the island and nearby locations, providing quick and flexible transit for your stay in the area.
Local Customs Options
- Crabbing Traditions: Engaging in local crabbing techniques is a cherished custom that connects visitors to the region's maritime heritage.
- Seafood Festivals: Participating in seasonal seafood festivals offers an authentic taste of the area's culinary culture rooted in its fishing community.
- Boat Etiquette: Respect for traditional boating customs ensures harmonious navigation and interaction among locals and visitors alike.
- Festive Celebrations: Observing community-specific holiday and seasonal events provides a glimpse into the area's unique local customs and camaraderie.
Frequently Asked Questions About Tylerton?
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:
- Chesapeake Waterfront with Private Dock in Crisfield, Maryland
- Welcome to the best view in Crisfield! top floor condo!
- IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
- Unique Tangier Cottage w/Chesapeake Bay Views!
- Come, sit back and relax at the "Catch of the Bay"
- Walk to Main Street: Family-Friendly Crisfield Gem
- Home of the Terrapin King
- Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island
- Unique Tangier Cottage with Chesapeake Bay Views!
- Walk to Main St Condo with Pool Access in Crisfield
2. How many vacation rentals have private pools in Tylerton?
There are 1 vacation rentals with private pools near Tylerton. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Tylerton are best for families?
If you are looking for a family-friendly vacation home in Tylerton, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Tylerton:
4. How many Rentbyowner vacation rentals are available in Tylerton?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 57 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.
5. What is the cancellation policy for vacation rentals in the area?
6. Are there any specific check-in and check-out times I should be aware of?
7. How do I ensure my reservation is secure when booking a vacation rental here?
8. What amenities are typically available in vacation rentals on this destination?
9. What should I do if I encounter issues during my stay in a vacation rental?
Tylerton Top Rated Vacation Rentals
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