See all properties
Entire home

Historic home on Smith Island w/ dock!

Photo gallery for Historic home on Smith Island w/ dock!

The Pearl built in 1900 restored 2015
Front
Living room
Living room notice the AC split unit!
Living room looking toward dining room and kitchen

Reviews

9.6 out of 10
Exceptional
3 bedrooms1+ bathroomSleeps 61200 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Outdoor Space

Explore the area

View in a map
Smith Island, MD
  • Place, Terrapin Sand Point
    ‪9 min walk‬
  • Place, Smith Island
  • Place, Patuxent River Naval Air Station

Rooms & beds

3 bedrooms (sleeps 6)

Captain's Quarters

1 Queen Bed

Guest Quarters

1 Queen Bed

Mate's Quarters

2 Twin 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.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet friendly
Air conditioning
Outdoor Space

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Deck
Walkable Beach Retreat on Chesapeake Bay!
  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
10.0 out of 10, Exceptional, (1 review)
Walkable Beach Retreat on Chesapeake Bay!

House Rules

Check in after 1:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
default

Children

Children allowed: ages 0-17
default

Events

No events allowed
default

Pets

Pets allowed: dogs and cats (limit 1 total)
The yard is not fenced, need to be leashed.
default

Smoking

Smoking is not permitted
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

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
Onsite 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 neighborhood

Ewell

Located in Smith Island, this vacation 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, motor boating, and fishing nearby, or enjoy the great outdoors with ecotours.
View more Vacation Homes in EwellOpens in a new window
Map
Smith Island, MD

What's nearby

  • Terrapin Sand Point - 9 min walk - 0.8 km

Restaurants

  • ‪Bayside Inn Restaurant - ‬6 min walk
  • ‪The Roost - ‬2 min walk
  • Drum Point Market
  • ‪Smith Island Baking Company - ‬8 min walk
  • ‪Smith Island Cake Store at the Bayside Inn Restaurant & Carryout - ‬6 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 Mar 26, 2026, prices found for a 1-night stay for 2 adults at Historic home on Smith Island w/ dock! on May 1, 2026 start from $192, 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?

Onsite 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!?

Check-out is at 10:00 AM.

Where is Historic home on Smith Island w/ dock! located?

Situated on the waterfront, this vacation home is 0.6 mi (0.9 km) from Terrapin Sand Point and 2.4 mi (3.9 km) from Smith Island.

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 34 out of 46 reviews
Rating 8 - Good. 12 out of 46 reviews
Rating 6 - Okay. 0 out of 46 reviews
Rating 4 - Poor. 0 out of 46 reviews
Rating 2 - Terrible. 0 out of 46 reviews

9.4/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

9.8/10

Check-in

10/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Sara L.

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

Smith Island Getaway

Very nice property! Spacious rooms, great host
Stayed 2 nights in Jun 2025
Verified

10/10 Excellent

Kristen W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

Harry L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house is wonderful, quaint and comfortable.The hosts are the best. Responsive and beyond helpful.
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Hugh

Liked: Cleanliness, amenities, property conditions & facilities, communication
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!
Stayed 2 nights in May 2025
Verified

10/10 Excellent

Rebecca K.

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

Relaxing stay

Great location for enjoying the island lifestyle. Everyone was super nice and helpful to make it a great experience.
Stayed 3 nights in Aug 2021
Verified

10/10 Excellent

Kenneth G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Aug 2025
Verified

8/10 Good

David L.

Liked: Check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

Gregory P.

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
Verified

10/10 Excellent

cate d.

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

perfect holiday

clean convenient and just what we wanted
Stayed 2 nights in Aug 2021
Verified

10/10 Excellent

Ralph

Liked: Cleanliness, amenities, property conditions & facilities, communication
Excellent property manager
Stayed 3 nights in Jul 2022
Verified

8/10 Good

loriane b.

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

Unique Vacation

We loved the simple, laid back vacation we had on Smith Island. One of the most unique vacations we have ever had. Everyone is so friendly and we enjoyed getting to know locals and other visitors as well. We plan to return.
Stayed 3 nights in Sep 2021
Verified

8/10 Good

Rachel N.

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

Couples get away

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.
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

Cheryl G.

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

Charm

Very close to everything we need to go to
Stayed 2 nights in May 2022
Verified

10/10 Excellent

Anthony M.

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

Beautiful property on Smith Island

The Pearl was a great property for us to enjoy an extended stay on Smith Island. We enjoyed the use of their bikes and kayak. Short walk from their dock and super helpful friends from the Capt Jason II to help us get to/from with our gear. We’re looking forward to coming back and sharing this place with some additional family soon!
Stayed 5 nights in Jul 2024
Verified

10/10 Excellent

Steve S.

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

Smith Island Trip

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!!
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Amanda K.

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

An amazing adventure!

Wonderful place to stay on Smith Island. For our family of four, the Pearl was plenty of space and very comfortable. We appreciated all the information about Smith Island sent ahead of time, including contacts for tours and coffee. Owner and operations manager were very friendly and answered all our questions. We would definitely stay here again!
Stayed 4 nights in Jul 2022
Verified

10/10 Excellent

Jordan N.

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

Great stay on Smith Island

Had a wonderful stay with. friend on Smith Island. Was just a special and unique place to visit. Leigh was very helpful and communicative. The house was sweet and cozy, and stocked with all our basic needs. Would definitely recommend!
Stayed 2 nights in Oct 2022
Verified

10/10 Excellent

Craig S.

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
Verified

10/10 Excellent

Mark H.

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

Perfectly amount of Peace and Quiet

The host was informative and very easy to chat too. The property was very clean and quant. We would recommend this stay to anyone looking to stay off the beaten path seeking peace and quiet with endless beauty surrounding ya.
Stayed 1 night in Jul 2022
Verified

10/10 Excellent

Grant T.

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

A fantastic experience

We came by boat from Annapolis, and what a great way to escape the hustle and bustle of the ”mainland!” The house is fantastic, the island is an amazing way to experience the way the Bay “once was”, and Chris and Leigh are phenomenal hosts. Will definitely be back! Side note - come by boat if you can!!
Stayed 1 night in Jun 2024
Verified

10/10 Excellent

Tom B.

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

Another wonderful getaway

This is our second time staying at the pearl and the air conditioning and screened in porch/deck improvements made the stay even more enjoyable than the first time. The house was clean, well kept and well stocked. Beds were soft and comfortable. Fishing was great. We will be back again for sure.
Stayed 3 nights in Aug 2024
Verified

10/10 Excellent

Sharen W.

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

Peaceful experience

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!
Stayed 3 nights in Sep 2024
Verified

8/10 Good

Adrienne R.

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
Verified

8/10 Good

Beth D.

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

Relax and enjoy

We had a wonderful, cozy stay at The Pearl on Smith Island! Our host shared everything we needed to know to get there and back without stress. The innkeeper was very nice and helpful too. We went kayaking and metal detecting on a nearby beach. We cruised the island on a golf cart. We ate lots of crab cakes, steamed crabs and Smith Island cake! If you are looking for a low-key, minimalist getaway- this is the perfect overnight! (Bring bug spray)
Stayed 2 nights in Aug 2024
Verified

10/10 Excellent

Tom B.

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

About the host

Hosted by Leigh and Chris Harte

Host profile image
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.

Languages:

English, Danish
Tell us how we can improve our siteShare feedback

Hotels

Vacation Rentals