3 bedroom/2.5 bath Smith Island bungalow with dock

Entire home in TYLERTON, Maryland

  1. 6 guests
  2. 3 bedrooms
  3. 4 beds
  4. 2.5 baths
Hosted by Dwight
  1. Superhost
  2. 11 years hosting

Listing highlights

Top 5% of homes

This home is highly ranked based on ratings, reviews, and reliability.

Outdoor entertainment

The firepit, alfresco dining, bbq area, and outdoor seating are great for summer trips.

Designed for staying cool

Beat the heat with the AC and portable fan.
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The Quietness of the island and the beautiful scenery around the waters edge. You will hear the birds and the waves and the wind. The island is void of loud noises, mostly nature. The home was built around 1860 and fully restored 2008. its perfectly imperfect!

The space
Located on the very quaint island of Tylerton, which makes up one of the 3 communities of Smith Island, MD . Enjoy the streets where there are no cars or trucks just the foot paths of the islanders. This home overlooks the harbor .

it is my personal home decorated with Island memories of my family that has lived on Smith Island for 400 years. ( founded 1608) I am a 16th generation native, the flow of the house leaves you with a feeling of completeness. Come in your own boat and tie up in front of the home and walk right up to the house. A fisherman's dream get away.

A fully appointed kitchen and utensils make the cooking experience even better.

The people, the seafood, is what draws people to DRUM POINT MARKET. You will find unique foods and their crab cakes are world renowned!!! The store has everything needed, except alcohol, leave the food home and get your supplies there.

the island is very small so biking and, walking are best on the pebble roads.

Make sure you contact me personally so that i can customize your trip to make it the best ever!!

MOST ASKED QUESTIONS:

Is there a grocery store? YES, its the only store on the island, DRUM POINT MARKET, but has everything and i mean everything, produce, seafood, canned goods, meats, cheeses etc.. It does NOT sell alcohol. Contrary to listings on the internet, The store hours are ONLY 10-3 monday through Saturday.

Where can we swim? The county dock is the best place to swim. It has ladders and the water is about 15 foot deep.

Is there church services on Sunday? Yes we are a Methodist community, but our services are compared to a non denominational service, ALL are welcome.

Do I have bikes or Kayaks? No bikes, but we have 2 kayaks for the guests to use. BUT Crisfield Kayaks will deliver kayaks to the boat for a fee if extras are needed. As for bikes, the island is very small and can be walked around in 10 minutes.

How far is the house from the Ferry or How do I get to the house? You are about 1 block from the main dock so usually walking is best.

What time does the ferries LEAVE the island? 7am daily and then again in the afternoon. call for ferry achedule. winter hours are subject to change

Do I need to bring linens, towels etc.? No, I charge a cleaning fee to accommodate this need, pack light.

Can I order seasonal seafood, more specifically oysters and crabs? Yes, please let me know upon your arrival to make the connection for you.

Other questions, please ask anyone you see everyone is very willing to help you out, don't be shy!!

Where is the WI FI password? is on the side of the refrigerator. Verizon is my provider and is not real great, usually you need to reboot daily. the modem is on the TV cabinet.

Can we arrive in our own boat? Yes I have a private dock in the harbor approximately 100 feet from the house, there is no electric or water connections for the boat.

Where do I catch the ferry . Capt. Larry Lairds ferry boat is docked at THE END of Main Street in Crisfield. This area is called the depot. His boat is named the CAPT JASON II. his phone number is (PHONE NUMBER HIDDEN).

Where do I leave my car? Ask Captain Larry for directions when you arrive

Guest access
The whole house is available to you.

Other things to note
This listing is a list of those things are that are available when you get there.

IF I WAS GOING TO SMITH ISLAND, THIS IS WHAT I WOULD DO OR SEE.

I would go see the pelicans ( arrange a tour with Eddie Corbin)
I would order crabs ( in season) to eat on the porch
I would take the tour of the whole island (Eddie Corbin) his card is at the house.
there are a few beaches ( Eddie Corbin can advise)
I would go to church if there on Sunday morning or Wednesday night
I would visit the other parts of the island ( Ewell and Rhodes Point )
I would visit the Crisfield/Smith Island Cultural Center in Ewell during the season ( May till Oct)
I would engage myself with the locals
I would fish off the docks
I would crab
I would definitely enjoy the sunsets
Schedule a painting class with Local artist, Dennis Clary, and take home an island original painting done by you!! you do not need to be an artist to paint. Dennis Supplies all of the materials (this is new to the island)

Where you’ll sleep

Bedroom 1
1 double bed
Bedroom 2
1 queen bed
Bedroom 3
2 single beds, 1 couch

What this place offers

Canal view
Bay view
Waterfront
Kitchen
Wifi

5 nights in TYLERTON

Jul 21, 2025 - Jul 26, 2025

Rated 4.96 out of 5 from 142 reviews.

Guest favorite
This home is in the top 5% of eligible listings based on ratings, reviews, and reliability
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Overall rating

  1. 5 stars, 96% of reviews
  2. 4 stars, 3% of reviews
  3. 3 stars, 1% of reviews
  4. 2 stars, 0% of reviews
  5. 1 stars, 0% of reviews

Rated 5.0 out of 5 stars for cleanliness

Rated 5.0 out of 5 stars for accuracy

Rated 5.0 out of 5 stars for check-in

Rated 5.0 out of 5 stars for communication

Rated 4.9 out of 5 stars for location

Rated 4.9 out of 5 stars for value

Where you’ll be

TYLERTON, Maryland, United States
This listing's location is verified.

Neighborhood highlights

A tiny hamlet in the middle of the Chesapeake Bay. a place to completely unwind and relax and breathe the fresh salt air...a place to just "get away from it all "

Meet your host

Superhost
142 reviews
4.96 out of 5 average rating
11 years of hosting
Where I went to school: Crisfield High School
My work: Insurance Agent
If you are looking for a great getaway "off the Grid" and want a boaters paradise, you have found the right location!!! I can create a great experience for you!!!

Dwight is a Superhost

Superhosts are experienced, highly rated hosts who are committed to providing great stays for guests.
To help protect your payment, always use Airbnb to send money and communicate with hosts.

Things to know

Cancellation policy
House rules
Check-in after 12:00 PM
Checkout before 7:00 AM
6 guests maximum
Safety & property
Carbon monoxide alarm
Smoke alarm