Skip to main content
Entire home

Historic home on Smith Island w/ dock!

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

Terrace/patio - Historic home on Smith Island w/ dock! (Smith Island)
Exterior - Historic home on Smith Island w/ dock! (Smith Island)
Beach - Historic home on Smith Island w/ dock! (Smith Island)
TV, books - Historic home on Smith Island w/ dock! (Smith Island)
Exterior detail - Historic home on Smith Island w/ dock! (Smith Island)
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 61200 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Outdoor space

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!

Along with laundry facilities, this smoke-free holiday home has tour/ticket assistance and a garden. Other amenities include barbecues. The holiday home has 3 bedrooms and offers a private yard and a patio. Guests will find a kitchen with a fridge, an oven, a stovetop and a microwave.
Air-conditioned accommodation at this holiday home offers coffee/tea makers and a hairdryer. Rooms open to patios. Kitchens offer fridges, stovetops, microwaves and kitchenware and utensils.

Bathrooms include a shower. Business-friendly amenities include desks and telephones.

The recreational activities listed below are available either on-site or nearby; fees may apply.

Property amenities

Internet

  • Available in the house: WiFi

Parking and transport

  • Parking on site

Kitchen

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

  • Smoke-free property

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

Restaurant
Best Western Plus Pocomoke City
  • Pool
  • Breakfast included
  • Parking included
  • Free Wi-Fi
8.6 out of 10, Excellent, 899 reviews
The price is HK$758
HK$849 total
includes taxes & fees
7 Mar - 8 Mar
Best Western Plus Pocomoke City
Compare similar properties

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
Information provided by the property may be translated using automated translation tools

Pets

Pets are 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 on 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
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
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 area

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. Visit our Ewell travel guide
View more Holiday homes in Ewell
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 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 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

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens 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

Cleanliness

9.6

Location

10

Property conditions & facilities

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

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

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

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

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

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

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

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

10/10 Excellent

Andy B.

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

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

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

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

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

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

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

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

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

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