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Historic home on Smith Island w/ dock!

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your current months are January, 2025 and February, 2025.
January 2025
February 2025

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

Beach
Terrace/patio
Exterior
Beach
Marina

Reviews

9.6 out of 10

Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 6111.5 sq m

Popular amenities

  • Parking available
  • Barbecue grill
  • Washer
  • Outdoor space
  • Pet-friendly
  • Kitchen

Explore the area

Map
Smith Island, MD
  • Smith Island
    20 min walk
  • Tylerton County Dock
    143 min walk
  • Smith Island Beans
    2 min walk
  • Bayside Inn Restaurant
    6 min walk

Room options

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.
During your stay at this vacation home, you'll be within walking distance of Terrapin Sand Point. The vacation home includes amenities such as a kitchen and 1.5 bathrooms.
  • Air-conditioned home with kitchen, washing machine, and 1.5 bathrooms
  • Services include tour or ticket assistance
  • 12.7 mi (20.5 km) from Great Hope Golf Course and 19.3 mi (31.1 km) from Chesapeake Health Care
This vacation home offers its guests barbecue grills, tour/ticket assistance, and a garden. The front desk is open around the clock.

Property manager

Leigh and Chris Harte

Languages

Danish, English

Property amenities

Internet

  • WiFi available

Parking and transport

  • On-site parking

Kitchen

  • Fridge
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Blender
  • Cookware/dishes/utensils
  • Electric kettle
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bed sheets provided

Bathrooms

  • 1.5 bathrooms
  • Shower
  • Soap
  • Towels provided
  • Toilet paper
  • Hairdryer

Living spaces

  • Living room

Entertainment

  • TV
  • Books

Outdoor areas

  • Patio
  • Garden
  • Barbecue
  • Garden
  • Dock

Laundry

  • Washing machine and dryer

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • 1 total pets
  • Welcoming cats and dogs only

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Tour/ticket assistance
  • Phone
  • Local meal delivery service

Location highlights

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

Things to do

  • Kayaking on site
  • Boating on site
  • Power boating nearby
  • Ecotours nearby
  • Kayaking nearby
  • Birdwatching nearby
  • Marina nearby
  • Fishing 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

  • Unit size: 1200 sq ft (111.5 sq m)

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

Pets

  • Pets are welcome
  • Only dogs and cats are allowed
  • Maximum 1 pets
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees
  • Note from host: The yard is not fenced, need to be leashed.

Children and extra beds

  • Children are welcome.

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.

We should mention

  • To make arrangements for your pet, contact the property directly using the information on your booking confirmation.

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

Historic home on Smith Island w/ dock! Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 26 out of 36 reviews" "
Rating 8 - Good. 10 out of 36 reviews" "
Rating 6 - Okay. 0 out of 36 reviews" "
Rating 4 - Poor. 0 out of 36 reviews" "
Rating 2 - Terrible. 0 out of 36 reviews" "

9.4/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

Reviews

10/10 Excellent

Sharen W.

Liked: Cleanliness
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

Tom B.

Liked: Cleanliness
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

8/10 Good

Beth D., williamsburg, VA

Liked: Cleanliness
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

Anthony M.

Liked: Cleanliness
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

10/10 Excellent

Grant T.

Liked: Cleanliness
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

Alyson M.

Liked: Cleanliness
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

10/10 Excellent

Craig S., Lusby, MD

Liked: Cleanliness
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.

Liked: Cleanliness
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.

Liked: Cleanliness
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.

Liked: Cleanliness
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.

Wonderful
Nice to settle down. We do wish the bikes and fishing equipment was better kept
Stayed 3 nights in Nov 2022

10/10 Excellent

Jordan N.

Liked: Cleanliness
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

Robert S.

Liked: Cleanliness
Great old house in Ewell suburbs
My wife and I visited Smith island for the people and natural surroundings, and we weren’t disappointed. The Pearl was a great base for our explorations. The owner was very helpful and responsive with our questions. Would definitely stay again.
Stayed 2 nights in Sep 2022

10/10 Excellent

Lisa W.

Liked: Cleanliness
Great place to relax.
Home was nice and clean and town people were friendly n helpful. Great place to come if you want to get away from it all like for reals everything.
Stayed 2 nights in Sep 2022

10/10 Excellent

Angela, Silver Spring

Liked: Cleanliness, amenities, property conditions & facilities
Stayed 3 nights in Aug 2022

10/10 Excellent

Kenneth B.

Liked: Cleanliness
Kicking it back, slowing down
First this place is remote, it's in the middle of the bay!!! The Pearl rocks, owner made contact about our visit, we were meet at the dock by our Inn Keeper, Ellie, she loaded our stuff and dropped us off and gave us island updates. If we needed something we called her. My Family and I Crabbed, Kayak and explored the island. If you have the mindset of "bait your own hook, clean your own fish, and make up your own lies" Then this place is a"Fit" for you. To thumbs up From the # britcherpaddleclub and # swatarasurfclub !!!! Ferries leave on time!!!
Stayed 4 nights in Aug 2022

8/10 Good

Jennifer G.

Liked: Cleanliness
Very Quiet Get-Away
The house is an interesting mix of new and old. The teens were able to connect their devices to the TV and watch Disney+, but in the evenings the internet can severely slow down (never was able to finish Cruella). Bedrooms were comfy, with window units, though the sheets were worn-out and need to be tossed. House needs a deep clean, there were cobwebs in corners and don't even look under the beds or sofa! Kitchen was well stocked with pots and pans, seasonings, oil, tea, and some condiments. We rode both bikes all over the island, and took out two of the kayaks. Be prepared to haul the kayaks down to the water and check the tides. Low tide means the water is shin deep for a decent distance from shore. The fishing kayak was missing a seat and paddle, so we couldn't take it out. Overall a good visit.
Stayed 4 nights in Jul 2022

10/10 Excellent

Amanda K., Alexandria, VA

Liked: Cleanliness
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

Ralph

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

10/10 Excellent

Pete S.

Liked: Cleanliness
Smith Island Anniversary Getaway
Our first visit to Smith Island was pleasant and relaxing. The Pearl was clean and comfortable and had everything we needed from a well stocked kitchen and bathrooms (bring your own toiletries) to bicycles and kayaks and window AC units. The sunsets were amazing and the lightning and thunderstorm was beautiful. We kayaked to Goat island and spotted pelicans, ospreys, cranes, turtles, crabs, numerous other birds and of course, goats. Meeting the kind and generous locals and other guests made the trip extra special. We did not get a chance to eat at The Bayside Inn as it was closed Monday and Tuesday or Tylerton, or to take the pelican tour, but we’ll make it a priority next visit. Thank you, Kim, for preparing such a delicious dinner for us! P.S. Bug spray is essential.
Stayed 2 nights in Jul 2022

10/10 Excellent

Mark H.

Liked: Cleanliness
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

Cheryl G., Va beach

Liked: Cleanliness
Charm
Very close to everything we need to go to
Stayed 2 nights in May 2022

8/10 Good

Matthew T.

Liked: Cleanliness
Quaint
Nicer house for the area. Kept clean. Enjoyed the stay. Town is pretty dilapidated. Need to clean up to maintain a tourist industry i would think.
Stayed 2 nights in Oct 2021

8/10 Good

loriane b.

Liked: Cleanliness
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

8/10 Good

Pat H.

Hot August Weekend
It’s what we expected. Nothing outstanding, but everything was fine. Could be cleaner, could be more updated...but was acceptable and as expected for the price. Bring plenty of bug spray. If you’re looking for quiet, solo time away from the rat race...this is your place. The restaurants on the island can be fickle, but as expected for a small island community. We explored and kayaked and my kids will remember it.
Stayed 3 nights in Aug 2021