House in Maryland
6 guests · 3 bedrooms · 1 bath
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Well priced for this locationPriced under area average
About this house rental
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.
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.
Amenities at Historic home on Smith Island w/ dock!
Non-smoking
Pets allowed
Family friendly
Map of Maryland
Ratings and reviews
8 / 10Excellent·Oct 2025
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.
10 / 10Outstanding·Aug 2025
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.
10 / 10Outstanding·Aug 2025
The house is wonderful, quaint and comfortable.The hosts are the best. Responsive and beyond helpful.
5 / 10·Jul 2022
The bad:
- The flies are aggressive. Bug spray required
- Basically no cell service, but there is WiFi / Internet
If you want to unplug this is the place to go. This is
the kind of location we were looking for to really get away
The Good:
- The host is great! We had to rent two houses because our
group was so big, The other house fell through and Chris
hooked us up with another house and saved our plans
- Smith Island is the friendliest place we have ever stayed.
Everyone says hello and stops to talk.
- Highly recommend you connect with one of the locals and
get a boat tour!
- The house was very nicely furnished and comfortable.
- Leigh and Chris are great hosts!
$$$$
Top rated by guests
9.6Outstanding
(47 Ratings)
"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 eve..."
Kenneth G.Don't miss out! Price and availability may change
