Smith Island Spectacular Sunsets!

Entire home hosted by Gretchen

  1. 11 guests
  2. 4 bedrooms
  3. 7 beds
  4. 2 baths
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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.

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

Air conditioning
Long term stays allowed
Unavailable: Carbon monoxide alarm

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4.80 out of 5 stars from 60 reviews


Where you’ll be

Smith Island, Maryland, United States

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!

Hosted by Gretchen

  1. Joined in September 2012
  • 157 Reviews
  • Identity verified
  • supporter
Our family includes two boys under 10 years and my husband and I. We love Baltimore and Smith Island, Maryland!
  • Language: English
  • Response rate: 80%
  • Response time: within a day
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Things to know

House rules

Health & safety

Airbnb's COVID-19 safety practices apply
Carbon monoxide alarm not reported Show more
Smoke alarm
Security Deposit - if you damage the home, you may be charged up to $500

Cancellation policy