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.
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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
Property # 2193588vb
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. 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.
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 10 May 2026, prices found for a 1-night stay for 2 adults at Historic home on Smith Island w/ dock! on 7 Sept 2026 start from AU$275, 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 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.
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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!
Great location for enjoying the island lifestyle. Everyone was super nice and helpful to make it a great experience.
Rebecca K.
Stayed 3 nights in Aug 2021
Response from VrboOwner on 9 Aug 2021
Rebecca thanks for staying and we hope to see you back soon!
Verified
10/10 Excellent
Hugh
22 June 2025
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!
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.
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.
loriane b.
Stayed 3 nights in Sep 2021
Response from VrboOwner on 19 Sept 2021
Thank you Loraine and we hope to see you back soon!
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!
Anthony M.
Stayed 5 nights in Jul 2024
Response from VrboOwner on 1 Aug 2024
Thank you Anthony! You clearly got the spirit of Smith Island :-) would love to have you back with your family and friends!
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.
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!
Amanda K.
Stayed 4 nights in Jul 2022
Response from VrboOwner on 6 Aug 2022
I'm particularly glad you enjoyed the Smith Island Kawffee! (coffee roasted on the Island). That is a real gem for any coffee aficionados. We are glad you enjoyed the visit and hope to see you again soon!
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!
Jordan N.
Stayed 2 nights in Oct 2022
Response from VrboOwner on 21 Oct 2022
Hi Jordan we can’t thank you enough for your kind words :-) we’re so glad that you enjoyed the island and felt the positive vibe. We hope to see you soon again!
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.
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.
Craig S.
Stayed 2 nights in May 2024
Response from VrboOwner on 14 May 2024
Thank you so much Craig! Glad it all worked out and we hope to see you on the Island again soon!
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!!
Grant T.
Stayed 1 night in Jun 2024
Response from VrboOwner on 19 July 2024
Grant please come back anytime! We commend you for coming to the island as the natives did over 400 years ago….by your own boat!
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.
Tom B.
Stayed 3 nights in Aug 2024
Response from VrboOwner on 9 Sept 2024
Thanks Tom glad you enjoyed the upgrades! We look forward to having you back again and again!
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!!
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!
Sharen W.
Stayed 3 nights in Sep 2024
Response from VrboOwner on 21 Sept 2024
Thank you! You and your family are terrific! Hope you can make it back soon!
Verified
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
Adrienne R.
Stayed 3 nights in Nov 2022
Response from VrboOwner on 13 Dec 2022
Thanks Adrienne! Glad you had a great time. Yea the bikes are suffering from a season of heavy use and will be redone for the beginning of the season.
Happy new year!
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)
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.
Tom B.
Stayed 3 nights in May 2023
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.