3 Br Private Vacation Home Vacation Rental In Smith Island, Maryland
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,...
Created Jul 20, 2026
1 Br Private Vacation Home Vacation Rental In Smith Island, Maryland
Relax in this 1910 era Smith Island home. Has one large upstairs bedroom with second twin bed separate from main bedroom. A short 3 minute walk from the ferry dock for the boat Island Belle II by...
Created Jul 20, 2026
3 Br Cottage Vacation Rental In Smith Island, Maryland
Unwind and relax after a busy life in the city. Our cozy cottage offers a comfortable and welcoming stay with everything you need for a laid back vacation.Awake refreshed and ready for a day of...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In Smith Island, Maryland
Welcome to this large, updated and well appointed home on Smith Island. This amazing property is situated on a large private lot and boasts 5 bedrooms. 2 bedrooms with king beds, 1 room with a...
Created Jul 20, 2026
2 Br Cottage Vacation Rental In Ewell, Maryland
From the moment you step off the ferry, you'll fall in love with Smith Island's rich history, car-free streets, and leisurely pace of life. This 'Castaway Cottage' vacation rental is the perfect...
Created Jul 20, 2026
2 Br Private Vacation Home Vacation Rental In Smith Island, Maryland
Welcome to Smith Island, MD, the village of Ewell a hidden gem in the heart of the Chesapeake Bay where time slows down and nature takes center stage. Accessible only by boat, this peaceful island...
Created Sep 14, 2025
3 Br Private Vacation Home Vacation Rental In Smith Island, Maryland
Come to Smith Island by your own boat or the several ferries that run daily. Experience the relaxation of the true island life. This quaint and charming 3BD/2BA beach cottage comes fully equipped...
Created Jun 8, 2025
