Historic home on Smith Island w/ dock!

Smith Island, Maryland
$271 avg/night
Minimum Stay 2 Nights
Bed 3

Bed

Bath 1

Bath

Home Private Vacation Home

Property Type

Sleep 6

Max Sleeps

Night 2 nights

Min Stay

The Pearl on Smith Island is a completely restored Eastern Shore farmhouse with the classic pitched roof. Built in 1900, the main level features a large railhead shower, a queen size bedroom, living room, dining room, and a well stocked comfortable kitchen that is open to the living room and dining room so guests can visit while making coffee or meals. The upstairs features a twin room with two twin beds and a large queen bedroom that overlooks the magnolia tree in the front yard. A half bath completes the upstairs. It’s a perfect place to kick back after a day on the water!

The dock is a short 4 minute walk from the house; fish, crab, and even moor your boat there! Some of the best fishing on the East Coast is around the Island-rockfish, speckled trout, cobia, redfish, croaker, and flounder. There are 3 kayaks for you to launch and explore the well documented kayak trails.

Accessible only by ferry, Smith Island is a unique experience; research Smith Island's rich history and historic culture on Wikipedia and YouTube, and then experience it for yourself! You will not get better softshell crabs or crab cakes anywhere! Rent a golf cart and drive through marshland to Rhodes Point and take a water taxi to Tylerton.

If you're not bringing your boat, we can help arrange a boat tour of the Smith Island archipelago and view pelican rookeries, the Martin Natural Preserve, and the many guts (creeks), which leads some to call it the Venice of the Chesapeake (with crab shanties instead of Italian Palazzos!).

Park your car in Crisfield, Maryland and take a relaxing 40 minute ferry to Smith Island, and the crew will get you and your things to the Pearl!

NOTE: Please let us know when booking if you are bringing your own boat for The Pearl Dock.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    1 Total Pets Pet Friendly Service Animals Exempt From Fees Welcoming Cats And Dogs Only
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Smoke Detector Not Reported (host Has Not Indicated Whether There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1200 Sq Ft (112 Sq M)
  • KITCHEN

    Coffee/tea Maker Dishwasher Electric Kettle Lobster/crab Pot Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Barbecue Grill Dock Garden Patio Yard
  • BATHROOMS

    1.5 Bathrooms Hair Dryer Shower Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk
  • LANGS SPOKEN

    Danish English
  • THINGS TO DO

    Birdwatching Nearby Boat On Site Ecotours Nearby Fishing Nearby Kayak On Site Kayaking Nearby Marina Nearby Power Boating Nearby
  • ENTERTAINMENT

    Books TV
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In A Village Near The Bay On The Waterfront
  • SERVICES AND CONVENIENCES

    Local Meal Delivery Service Phone Tour/ticket Assistance
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 01:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Availability

Review Review

  • Hugh

    Submitted Jun 22, 2025

    Stayed May 31, 2025

    This property was perfect for a family of 4. It was very clean, the kitchen was well stocked and the neighbors were amazing and helpful. Visit the arcade by the marina right before sunset!

  • Ralph

    Submitted Jul 21, 2022

    Stayed Jul 17, 2022

    Excellent property manager

  • Nina Z.

    Submitted May 27, 2026

    Stayed May 23, 2026

    Great place on Smith Island. Amazing community feeling for 48 hours. The ferry is super expensive (it was 25 per person each way ,so 50 total per person!!!), adding 250 to the entire visit for 5, so something to really consider. The island is beautiful, house was perfect, very quiet and well kept. No downsides, but not tons of activities for very active teenagers. Everything super easy in terms of house/info/check in and out.

  • David L.

    Submitted Oct 3, 2025

    Stayed Sep 29, 2025

    We enjoyed ourselves besides the weather that turned bad, fall is not the best time to visit Smith Island, everything was operating on limited hours.

  • Kenneth G.

    Submitted Aug 16, 2025

    Stayed Aug 8, 2025

    The house was perfect for a quiet, long weekend of fishing and relaxing. Smith Island is a unique get-away with a small town charm and welcoming residents who made us feel like home. The Pearl had everything we needed with comfortable accommodations given the relative seclusion of the island. Leigh and Chris were extremely responsive.

  • Harry L.

    Submitted Aug 14, 2025

    Stayed Aug 11, 2025

    The house is wonderful, quaint and comfortable.The hosts are the best. Responsive and beyond helpful.

  • Rachel N.

    Submitted Jul 27, 2025

    Stayed Jul 25, 2025

    We arrived via our private boat. We were welcomed in a timely manner by the smiling innkeeper, who escorted us from dock to the Pearl. We enjoyed our stay, the house was quaint and just a short walk to the boat. Most of our trip comprised of fishing- we caught nearly all blue fish, and even had a delicious fish meal one night from our catch! The town is small, has a nice little museum and coffee shop. We enjoyed the smith island cake too! Make sure you bring bug spray, your own groceries and alcohol.

  • Sara L.

    Submitted Jul 27, 2025

    Stayed Jun 20, 2025

    Very nice property! Spacious rooms, great host

  • Steve S.

    Submitted Jul 21, 2025

    Stayed Jul 7, 2025

    The owner and host were Great!! The property was pretty perfect and even nicer than i expected. Getting there was easy from the boat ride to being brought to the property. The Captain of the Jason is right across the street and his wife manages the property. There were 6 of us and from using the bikes, renting a golf cart and walking it was super easy getting around. My brother and I kayaked across to an Island near the inlet with the kayaks on property and it is beautiful there. Looks like great fishing at the right time of year. All the seafood was spot on!!

  • Kristen W.

    Submitted Jul 18, 2025

    Stayed Jul 4, 2025

    The hosts did an EXCELLENT job of communicating before and during our stay. They made great recommendations for local activities and food. The house had everything we needed for our stay, and the AC worked like a champ! We would absolutely recommend a stay at the Pearl!

  • Erinn C.

    Submitted Jul 15, 2025

    Stayed Jun 28, 2025

    We had a wonderful stay at The Pearl. The house is well appointed, clean, comfy and a great location on the island. Our hosts answered all of our questions and provided lots of helpful information. New TV worked great (with our own Samsung login). Cell service is spotty on the island, but who needs it? Wifi worked fine for streaming movies and shows, too. The trip over on the Captain Jason was seamless and we had all of our belongings dropped off at the house for us. We ordered steamed crabs from Captain Kitching (delicious) and sadly we had to miss our sunset cruise with Capt Pat because of rain (no hard feelings against the Capt at all!). Neighbors are nice. Doggies are nice. Ducks are nice. Go stay at the Pearl to relax and unwind. And eat all the Smith Island Cake.

  • Sharen W.

    Submitted Sep 19, 2024

    Stayed Sep 2, 2024

    The location was perfect, our host was extremely responsive and helpful. Chris gave us tips and set us up with the ferry Captain. Even though the large restaurant was closed there are 2 chefs that prepare wonderful meals! The srore/museum was ooen go meet the sweet manager! Thank you Chris for a wonderful family vacation!

Your dates are Available!

Total

Includes taxes and fees
$271+
View details