Title: Historic home on Smith Island w/ dock! - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&selected=63942827&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) 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! ![Terrace/patio - Historic home on Smith Island w/ dock! (Smith Island)](https://images.trvl-media.com/lodging/64000000/63950000/63942900/63942827/f202aa27.jpg?impolicy=resizecrop&rw=598&ra=fit) ![TV, books - Historic home on Smith Island w/ dock! (Smith Island)](https://images.trvl-media.com/lodging/64000000/63950000/63942900/63942827/07d10997.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior detail - Historic home on Smith Island w/ dock! (Smith Island)](https://images.trvl-media.com/lodging/64000000/63950000/63942900/63942827/83e49b48.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior - Historic home on Smith Island w/ dock! (Smith Island)](https://images.trvl-media.com/lodging/64000000/63950000/63942900/63942827/f1e4c7de.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Beach - Historic home on Smith Island w/ dock! (Smith Island)](https://images.trvl-media.com/lodging/64000000/63950000/63942900/63942827/05e059a6.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies 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 Exceptional ### Entire home 3 bedrooms2 bathroomsSleeps 61200 sq ft ## Popular amenities - Kitchen - Washer - Dryer - Outdoor Space ## Add dates for prices Check-in Check-out Travellers ## 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 ![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110150000/110145700/110145636/e23353a2.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island Smith Island - Kitchen - Washer - Dryer - Pet friendly 10 Exceptional 1 review [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-03&endDate=2026-02-04&selected=110145636&PinnedHotelID=110145636&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/72000000/71470000/71467900/71467811/024eac30.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK Smith Island - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 18 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-03&endDate=2026-02-04&selected=71467811&PinnedHotelID=71467811&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87740000/87738300/87738255/15de662d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Come, sit back and relax at the "Catch of the Bay" Crisfield - Kitchen - Washer - Dryer - Pet friendly 10 Exceptional 6 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-03&endDate=2026-02-04&selected=87738255&PinnedHotelID=87738255&HadPinnedHotel=true®ionId=-1&adults=2) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/93000000/92750000/92745600/92745551/ac31e97d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Come escape to Smith Island for the winter and enjoy nature, peace and quiet Smith Island - Kitchen - Washer - Dryer - Pet friendly 9.8 Exceptional 15 reviews CA $250 CA $402 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-28&endDate=2026-01-29&selected=92745551&PinnedHotelID=92745551&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/76000000/75700000/75693000/75692925/ab7d0ec2.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Cottage near the Bay Crisfield - Kitchen - Dryer - Pet friendly - Free WiFi 8.8 Excellent 52 reviews CA $112 CA $260 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-21&endDate=2026-01-22&selected=75692925&PinnedHotelID=75692925&HadPinnedHotel=true®ionId=-1&adults=2) ![Cottage (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/105000000/104400000/104396400/104396390/5165f1ee.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Pet-friendly Smith Island Cottage w/ Golf Cart! 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Deal Island - Kitchen - Washer - Dryer - Pet friendly 10 Exceptional 2 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-03&endDate=2026-02-04&selected=106502692&PinnedHotelID=106502692&HadPinnedHotel=true®ionId=-1&adults=2) ## 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 ### 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 area Located in Smith Island, this vacation 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, motor boating, and fishing nearby, or enjoy the great outdoors with ecotours. [Visit our Ewell travel guide](https://www.expedia.ca/Ewell.dx3000440567) [View more Vacation homes in Ewell](https://www.expedia.ca/Ewell-Private-Vacation-Homes.d3000440567-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C37.99507%2C-76.03563&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=Vymth5p5e0vReTEPQnd5u_QXujQ=) 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? ### How much is parking? ### What time is check-in at Historic home on Smith Island w/ dock!? ### What time is check-out at Historic home on Smith Island w/ dock!? ### Where is Historic home on Smith Island w/ dock! located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## 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 information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 34 8 - Good 12 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 9.4 Cleanliness ### 9.6 Location ### 10 Property conditions & facilities ## Reviews ### 10/10 Excellent #### Sara L. Jul 27, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Smith Island Getaway Very nice property! Spacious rooms, great host ##### Sara L. Stayed 2 nights in Jun 2025 ### 10/10 Excellent #### Kristen W. Jul 18, 2025 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! ##### Kristen W. Stayed 2 nights in Jul 2025 ### 10/10 Excellent #### Hugh Jun 22, 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! ##### Hugh Stayed 2 nights in May 2025 ### 10/10 Excellent #### Anthony M. Jul 25, 2024 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! ##### Anthony M. Stayed 5 nights in Jul 2024 ### 10/10 Excellent #### Craig S. May 13, 2024 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. ##### Craig S. Stayed 2 nights in May 2024 ### 10/10 Excellent #### Tom B. Aug 19, 2024 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. ##### Tom B. Stayed 3 nights in Aug 2024 ### 10/10 Excellent #### Grant T. Jul 11, 2024 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!! ##### Grant T. Stayed 1 night in Jun 2024 ### 10/10 Excellent #### Sharen W. Sep 19, 2024 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! ##### Sharen W. Stayed 3 nights in Sep 2024 ### 8/10 Good #### Beth D. Aug 5, 2024 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) ##### Beth D. Stayed 2 nights in Aug 2024 ### 10/10 Excellent #### Alyson M. Jun 6, 2024 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! ##### Alyson M. Stayed 3 nights in May 2024 ### 10/10 Excellent #### Andy B. Sep 5, 2023 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. ##### Andy B. Stayed 3 nights in Sep 2023 ### 10/10 Excellent #### Harry L. Aug 14, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy The house is wonderful, quaint and comfortable.The hosts are the best. Responsive and beyond helpful. ##### Harry L. Stayed 3 nights in Aug 2025 ### 10/10 Excellent #### Kenneth G. Aug 16, 2025 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. ![](https://a.travel-assets.com/ugc/hotel-reviews/8b7b2a43-5844-447a-948e-4417b0a6d7b3-1755382051811.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/2bb072d3-26e8-43db-8643-39140d895f11-1755382050050.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/04730ff4-8934-467d-aee2-712acea22ee1-1755382049855.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/5452859c-065b-434a-ac23-f05094b2f20e-1755382050746.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ##### Kenneth G. Stayed 3 nights in Aug 2025 ### 8/10 Good #### David L. Oct 3, 2025 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. ##### David L. Stayed 3 nights in Sep 2025 ### 10/10 Excellent #### Rebecca K. Aug 9, 2021 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. ##### Rebecca K. Stayed 3 nights in Aug 2021 ### 8/10 Good #### Rachel N. Jul 27, 2025 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. ##### Rachel N. Stayed 2 nights in Jul 2025 ### 10/10 Excellent #### Gregory P. Jul 14, 2023 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. ##### Gregory P. Stayed 2 nights in Jul 2023 ### 10/10 Excellent #### cate d. Aug 26, 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### perfect holiday clean convenient and just what we wanted ##### cate d. Stayed 2 nights in Aug 2021 ### 10/10 Excellent #### Ralph Jul 21, 2022 Liked: Cleanliness, amenities, property conditions & facilities, communication Excellent property manager ##### Ralph Stayed 3 nights in Jul 2022 ### 10/10 Excellent #### Steve S. Jul 21, 2025 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!! ##### Steve S. Stayed 3 nights in Jul 2025 ### 8/10 Good #### loriane b. Sep 19, 2021 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. ##### loriane b. Stayed 3 nights in Sep 2021 ### 10/10 Excellent #### Cheryl G., Va beach May 30, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Charm Very close to everything we need to go to ##### Cheryl G. Stayed 2 nights in May 2022 ### 10/10 Excellent #### Amanda K., Alexandria, VA Jul 30, 2022 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! ##### Amanda K. Stayed 4 nights in Jul 2022 ### 10/10 Excellent #### Jordan N. Oct 19, 2022 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! ##### Jordan N. Stayed 2 nights in Oct 2022 ### 10/10 Excellent #### Mark H. Jul 11, 2022 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. ##### Mark H. 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