Smith Island Spectacular Sunsets!

Entire home in Smith Island, Maryland

  1. 11 guests
  2. 4 bedrooms
  3. 7 beds
  4. 2 baths
Rated 4.82 out of 5 stars.84 reviews
Hosted by Gretchen
  1. Superhost
  2. 13 years hosting

Listing highlights

Designed for staying cool

Beat the heat with the AC and portable fan.

Exceptional check-in experience

Recent guests gave the check-in process a 5-star rating.

Peace and quiet

This home is in a quiet area.
Historic large four bedroom waterfront home on lovely Smith Island. Journey back in time to a simpler way of life- living off the bounty of the land and waters of the Chesapeake Bay.

The space
Gorgeously appointed and newly renovated large historic four bedroom, two story home, on the water in Tylerton, Smith Island, Maryland in the heart of the beautiful Chesapeake Bay. Affectionately called "Pauline's House" in honor of the first owner, the house comfortably sleeps 9, with 2 queen size beds, 5 single beds and one toddler bed (additional beds available upon request)- perfect for large groups of friends or families.

Spacious eat in kitchen, PLUS a dining room- total seating for 12-16. Spectacular waterfront views from dining room, kitchen and three bedrooms. Lovely sunlit living room, two full bathrooms and a full mudroom with a washer and dryer.

Large backyard on the water with white picket fence for the little ones, and a vegetable garden for picnicing, barbequing and lounging.

All bedroom and bathroom linens provided, as well as all the kitchen supplies one might need(cookware, dishes, glassware, etc.) if you'd like to cook while on the island.

Alternatively, if you would like the B and B experience, we can arrange for your meals (breakfast, lunch and/or dinner) to be expertly prepared and delivered by island ladies- to your custom order (see "Other Things to Note" section).

Children 5 and under stay for free, and age 6-12 are only $25 a night.

Guest access
The entire home and yard will be yours during your stay.

Other things to note
- Delicious Meals Cooked by Island Ladies and Delivered to you: Kristen Corbin (the most amazing baked applesauce in the world!) can be reached at 410-425-2177 or 410-603-8173. Joan Corbin- delicious dishes as well! Both ladies can provide you with full meals for breakfast, lunch and dinner if you call and arrange it ahead of time (or we can arrange it for you). AND- do let them know if you'd like crabs or oysters harvested fresh from the bay and they will ask the waterman to harvest just for you- eating crabs and oysters straight off the boat has been the most extraordinary experience in food we've ever had!
-Boat rides to the Pelican Rookery, Ewell/Rhodes Point, or beachcombing ("progging" pronounced with a long "o"): Eddie Corbin, Missy Evans (410-968-1175), Barry Bruce (410-425-3181), or Dwight Marshall (410-425-2023)
- Fishing or Duck Hunting during season: Chris Marshall (410-968-0175)
-Crabbing or Oyster Harvesting (i.e. you go on the boat with him, visit a crab shanty, etc.): Barry Bruce (410-425-3181)
- You are welcome to bring alcoholic beverages with you, but please be somewhat discrete as the island is "dry"
-Canoe or Kayak Rentals- call in advance, and they can meet you with the canoe(s) or kayak(s) at the dock in Crisfield when you are getting on the ferry, and will pick them back up from the ferry when you return. All phone numbers are available upon request once a reservation has been made for the house, as Airbnb blocks phone numbers prior to a reservation being made.

Where you’ll sleep

Bedroom 1
1 queen bed, 1 single bed
Bedroom 2
2 single beds, 1 toddler bed
Bedroom 3
1 queen bed

What this place offers

Waterfront
Kitchen
Washer
Dryer
Air conditioning
Unavailable: Carbon monoxide alarm

5 nights in Smith Island

Jul 21, 2025 - Jul 26, 2025

4.82 out of 5 stars from 84 reviews

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Overall rating

  1. 5 stars, 83% of reviews
  2. 4 stars, 15% of reviews
  3. 3 stars, 1% of reviews
  4. 2 stars, 0% of reviews
  5. 1 stars, 0% of reviews

Rated 4.8 out of 5 stars for cleanliness

Rated 4.9 out of 5 stars for accuracy

Rated 4.9 out of 5 stars for check-in

Rated 4.7 out of 5 stars for communication

Rated 4.8 out of 5 stars for location

Rated 4.7 out of 5 stars for value

Where you’ll be

Smith Island, Maryland, United States
This listing's location is verified and the exact location will be provided after booking.

Neighborhood highlights

Where is Tylerton, Smith Island? Just a short ferry ride from Crisfield, Maryland- travel back in time with your family and friends to this quaint and blissfully quiet traditional waterman's village. Enjoy kayaking, boating, hiking, fishing, crabbing, harvesting oysters, beachcombing (called "progging" by the locals), biking or simply taking long contemplative walks along the water. For hunters and fisherman, there is some of the best duck hunting and fishing on the East Coast! Amateurs can also fish or crab right off the public dock, or you can hire a local waterman to take you out on the water (see "Other Things to Note" section for contacts).

Visit the local Drum Point Market for the world's absolute best crab cakes, or take a stroll along the crab shanty dock and visit local toy and craftmakers. Visit the famous crab picking coop, and play baseball, soccer and lacrosse and fly kites on the baseball field. Explore the incredible Pelican Rookery (right out of National Geographic!) and take a trip to a crab shanty to learn how hard shell crabs become soft shells! Spend time leisurely talking to locals all about the island's history and their life on the island. Become an honorary Junior Fire Fighter at the local fire station, or just spend luxurious hours sitting on the dock, watching the tide ebb and flow, and eventually, the spectacular setting sun. Then watch in awe as the dark night sky comes alive with thousands of brilliantly beaming stars just for you!

Meet your host

Superhost
227 reviews
4.82 out of 5 average rating
13 years of hosting
Speaks English
Lives in Baltimore, Maryland
Our family includes two boys under 15 years, and my husband and I. We love Baltimore, Annapolis and Smith Island, Maryland!

Gretchen is a Superhost

Superhosts are experienced, highly rated hosts who are committed to providing great stays for guests.

Host details

Response rate: 100%
Responds within a few hours
To help protect your payment, always use Airbnb to send money and communicate with hosts.

Things to know

Cancellation policy
House rules
11 guests maximum
Safety & property
Carbon monoxide alarm not reported
Smoke alarm
Pet(s) live on property