Historic home on Smith Island w/ dock!

3 bedrooms1+ bathroomSleeps 6111.5 sq m

Popular amenities

Pet-friendly

Hot tub

Kitchen

Barbecue grill

Washer

Dryer

Explore the area

Smith Island, MD

Terrapin Sand Point11 min walk
Smith Island20 min walk

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

About this property

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.

Property manager

Leigh and Chris Harte

Premier Host

Languages

Danish, English

Amenities

Hot tub

Kitchen

Washer

Dryer

Pet-friendly

Air conditioning

Kitchen

Washer

Dryer

Air conditioning

House Rules

Check in after 1:00 PM

Minimum age to rent: 21

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed: dogs and cats (limit 1 total)

The yard is not fenced, need to be leashed.

Smoking

Smoking is not permitted

If you are bringing your boat to moor at The Peal Dock, please let us know when you book.

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

Important information

You need to know

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. Great Hope Golf Course and Somers Cove Marina 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 Terrapin Sand Point. Discover the area's water adventures with kayaking, power boating and fishing nearby, or enjoy the great outdoors with ecotours.

Smith Island, MD

What's nearby

Terrapin Sand Point - 11 min walk
Smith Island - 20 min walk

Restaurants

Bayside Inn Restaurant - 6 min walk
Smith Island Baking Company - 8 min walk
Smith Island Beans - 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).

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 0.6 mi (0.9 km) from Terrapin Sand Point and 2.4 mi (3.9 km) from Smith Island. Great Hope Golf Course and Chesapeake Health Care are also within 20 miles (32 km).

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

9.4/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

9.6/10

Check-in

10/10

Communication

9.6/10

Location

9.6/10

Listing accuracy

10/10 Excellent

Craig S.

13 May 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Smith Island Getaway

This was a perfect spot for out three-generation getaway. Property was a perfect fit for us and the new deck with screened-in porch is a great addition to this property. Well stocked kitchen made meal prep a breeze, and the gas grill came in very handy. Comfy furniture and a great dining room table perfect to game night.

Stayed 2 nights in May 2024

10/10 Excellent

Andy B.

5 Sept 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Labor Day Layover

This was one of the most relaxing stays the family has ever had. Who can argue with Smith Island Cake from the bakery for breakfast!! The house was a great little hideaway to celebrate a 14th birthday and a 23rd anniversary. Having easy access to a boat dock allowed us to bring our own boat and so the freedom to fish the waters surrounding Smith Island, an afternoon trip to Tylerton for the absolute delicious crab cakes and a chat with Duke, a day trip to Crisfield for the annual boat docking competition, and sunset cruises and amazing stargazing. The highlight and “most awesome thing ever” said the 14 year old, was a personal Smith Island Cake making class with Donna and Phil. Our biggest tip is Bring your bug spray and if you use the dock, your deck boots — extreme tides cover the lane from the dock to the main road.

Stayed 3 nights in Sep 2023

10/10 Excellent

Gregory P.

14 July 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for groups/clubs !

Have been to Smith Island many times and will return ! Great place for kayaking. Locals are very friendly and helpful.

Stayed 2 nights in Jul 2023

10/10 Excellent

Tom B.

2 June 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peace and Plenty of Fish

Clean, cozy, well stocked. Nice kitchen and dining room for home cooked meals since there aren't too many breakfast and dinner dining options on the island. Locals were nice including Mark who got us bait. We caught plenty of fish and cooked them too. Wi Fi worked well. Bedrooms and baths were clean and cozy. Owners were responsive to all my questions. Will definitely be back.

Stayed 3 nights in May 2023

8/10 Good

Adrienne R.

8 Dec 2022

Liked: Communication, location

Disliked: Check-in

Wonderful

Nice to settle down. We do wish the bikes and fishing equipment was better kept

Stayed 3 nights in Nov 2022

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.