Skip to main content
Entire home

Historic home on Smith Island w/ dock!

Waterfront vacation home with kitchen and patio

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

Beach
3 bedrooms, desk, WiFi, bed sheets
Terrace/patio
Marina
Exterior
Escape to The Pearl on Smith Island, a beautifully restored 1900 Eastern Shore farmhouse. Enjoy the well-stocked kitchen and living room or explore the nearby dock within a short walk, where you can fish or launch one of three kayaks.

Reviews

9.6 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 6112 sq m

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Barbecue grill

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.

Property amenities

Internet

  • Available in the house: WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Lobster/crab pot
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 1.5 bathrooms
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • TV

Outdoor areas

  • Barbecue grill
  • Dock
  • Garden
  • Patio
  • Yard

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming cats and dogs only
  • One pet total

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Meal delivery service
  • Phone
  • Tour and ticket assistance

Location highlights

  • In a village
  • Near the bay
  • Near the marina
  • On the waterfront

Things to do

  • Boat
  • Kayak
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Kayaking nearby
  • Motor boating nearby

Safety features

  • 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)

General

  • Garden
  • Unit size: 1,200 square feet

Similar properties

Smart TV, fireplace, table tennis, books
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
9.8 out of 10, Exceptional, 15 reviews
The price is AED 731
AED 1,152 total
includes taxes & fees
19 Nov - 20 Nov
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Policies

Check-in

Check-in time starts at 1:00 PM
Minimum check-in age: 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Rules

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

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs and cats only
1 total pets
Restrictions apply; for more information contact the property at the number on the booking confirmation
Note from host: The yard is not fenced, need to be leashed.

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

Historic On Smith W Dock Smith
Historic Home on Smith Island w/ Dock! Smith Island
Historic Home on Smith Island w/ Dock! Private vacation home

About the neighborhood

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
  • ‪Ruke's General Store and Seafood Deck - ‬4 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 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.

Have a question?

AI iconBeta

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

Historic home on Smith Island w/ dock! Reviews

Reviews

9.6

Exceptional

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

8.0/10

Eco-friendliness

Reviews

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

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

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

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

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

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

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

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

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

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

10/10 Excellent

Ralph

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

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

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

10/10 Excellent

Cheryl G., Va beach

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

Charm

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

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

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

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

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

10/10 Excellent

Amanda K., Alexandria, VA

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

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

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

10/10 Excellent

Erinn C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in Jun 2025

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

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

10/10 Excellent

Alyson M.

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

Wonderful island get away!!

During our stay at The Pearl, we encountered our own boat issues, but the hosts were extremely helpful. Their communication was above and beyond!! The people on the island were also extremely helpful, and they went out of their way to help in any way they could. They all truly wanted us to have a great experience on Smith Island. The Pearl had everything we needed for our stay, and there was plenty of room for us. We took our pet Corgi and she felt right at home and loved the big yard! We CANNOT wait to go back!
Stayed 3 nights in May 2024