Top-rated for comfort — guests feel right at home here.
Centrally-located
You're never far from where you need to be with this convenient location.
3 bedrooms1+ bathroomSleeps 6
Popular amenities
Onsite parking available
Dogs and cats allowed
Kitchen
Washing machine
Air-conditioning
Barbecue grill
Explore the area
Smith Island, MD
Rooms & beds
3 bedrooms (sleeps 6)
Captain's Quarters
1 Queen Bed
Guest Quarters
1 Queen Bed
Mate's Quarters
2 Single Beds
1 bathroom, 1 half bathroom
Lower Deck Head
Toilet · Shower only
Upper Deck Head
Toilet
Spaces
Deck or patio
Kitchen
Garden
Dining area
About this property
Historic home on Smith Island w/ dock!
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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If you are bringing your boat to moor at The Peal Dock, please let us know when you book.
Important information
You need to know
Property # 2193588vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
About the area
Ewell
Located in Smith Island, this holiday home is on the waterfront. Tylerton County Dock and Crisfield City Dock are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Smith Island and Thorofare Island. Discover the area's water adventures with kayaking, power boating and fishing nearby, or enjoy the great outdoors with ecotours.
Smith Island Cake Store at the Bayside Inn Restaurant & Carryout - 6 min walk
The Roost - 2 min walk
Frequently asked questions
Is Historic home on Smith Island w/ dock! pet-friendly?
Yes, this property allows cats and dogs (limit 1 total). Some restrictions may apply, so please contact the property for more details.
How much does it cost to stay at Historic home on Smith Island w/ dock!?
As of 30 Aug, 2026, prices found for a 1-night stay for 2 adults at Historic home on Smith Island w/ dock! on 4 Nov, 2026 start from S$385, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Historic home on Smith Island w/ dock!?
On-site parking is available at the property.
What time is check-in at Historic home on Smith Island w/ dock!?
Check-in begins at 1:00 PM.
What time is check-out at Historic home on Smith Island w/ dock!?
Checkout is at 10:00 AM.
Where is Historic home on Smith Island w/ dock! located?
Situated on the waterfront, this holiday home is 2.4 mi (3.9 km) from Smith Island.
About the host
Hosted by Leigh and Chris Harte
The Harte's have lived around the world, and for the last 10 years, settled in the Washington DC area. Chris Harte and his Dad fell in love with Smith Island 10 years ago when traveling there on their boat, and recently bought the Pearl with dock as a base for enjoying boating, fishing, kayaking, crabbing, and other watersports of the Chesapeake Bay.
Why they chose this property
*So Close, Yet a World Away!*
Take the scenic 3 hour drive over the Bay Bridge from DC, or down the Eastern Shore from Philly/NJ/NYC, and come to a different world. As soon as you get on the ferry to Smith Island, your adventure begins. (detailed ferry instructions will be sent when you book, or inquire)
Smith Island is the last and only populated island in Maryland with no bridge access. Settled in 1670 by English settlers, the descendants still reside there and work the Chesapeake Bay as watermen.
Sometimes called the Venice of the Chesapeake, Smith Island is actually an archipelago, with 3 towns, capped by the Martin Nature Preserve to the north.
The Preserve has multiple pelican rookeries, and even a snow egret rookery. You can tour through the guts (creeks) and see preserved Chesapeake marshland.
We also challenge you to find a better crab cake, softshell crab, or oyster than what's served on the Island!
Enjoy the Island's unique combination of history (Native American relics are even found on the Island), Chesapeake nature, watersports (fishing, crabbing, kayaking, boating), and relaxing atmosphere.
What makes this property unique
*Top 5 Reasons To Stay on Smith Island*
1. Visit Maryland's last inhabited remote island, with a culture going back 400 years, with a waterman's way of life that is fast disappearing elsewhere 2. Fishing and crabbing: it is centrally located in the Bay to access Tangier Sound, the Middle and Lower Chesapeake Bay, and shallow water fishing in the Smith Island archipelago, within minutes See if you can score the Smith Island Grand Slam during you visit: Rockfish, Bluefish or Spanish Mackerel, Redfish, Cobia, and Speckled Trout. As a local Smith Islander said to us once, "you start your fishing trip already in the middle of the Bay". 3. Kayak the well marked water trails, and get Zen with the Island's nature 4. Enjoy local seafood at the restaurants, including the best crab dishes you’ll ever try, add a slice of the famous Smith Island cake 5. Relax at the Pearl and enjoy it’s nature, it’s Waterman culture, and 400 year history
*For Anglers*
We encourage you to think about Smith Island as your fish camp. Take your own boat to the Island and be in the middle of the action. You can fish deep water in the Bay and the Sound, or fish the flats and shallows of the Smith Island archipelago. At the right time of the year, you can catch up to 10 species of game fish! Try you skill and see if you can achieve the Smith Island Slam (Rockfish, Bluefish, Redfish) or a Grand Slam (Rockfish, Bluefish, Redfish, Cobia, and Speckled Trout). Then, come back to the Island, enjoy a crab dinner or just cook what you caught.
Don’t have a boat or easy access to take yours there? No problem, book with one of the professional local guides who will pick you up at the main dock and take you on your fishing journey.
Have your own boat with sleeping quarters? Book the Peal Dock and overnight there.
Staying on Smith Island will provide an experience of a lifetime.