Smith Island Travel Guide
Tourist Guide
Visit Smith Island
Historic home on Smith Island w/ dock!
Smith Island, MD
Stay at this holiday home in Smith Island. Enjoy a garden, laundry facilities and patios. Popular attractions Smith Island and Tylerton County Dock are located ...
9.4/10 Exceptional! (43 reviews)
"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 ..."
Reviewed on 16 Aug 2025
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Ewell, MD
Stay at this cottage in Smith Island. Enjoy laundry facilities, an in-room coffee maker and air conditioning. Popular attractions Smith Island and Tylerton County ...
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Smith Island, MD
The price is £262 per night from 2 Sept to 3 Sept
£262
2 Sept - 3 Sept
includes taxes & fees
Stay at this holiday home in Smith Island. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Smith Island and Tylerton County Dock are located ...
9.6/10 Exceptional! (10 reviews)
"Great stay, Christopher was accommodating. Great place for 2-3 people. Golf cart was a great add on. Friendly neighbors. Very short walk from boat ( use green boat) Otis"
Reviewed on 28 Jul 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Historic home on Smith Island w/ dock!
Smith Island, MD
Stay at this holiday home in Smith Island. Enjoy a garden, laundry facilities and patios. Popular attractions Smith Island and Tylerton County Dock are located ...
9.4/10 Exceptional! (43 reviews)
"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 ..."
Reviewed on 16 Aug 2025
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Smith Island, MD
Stay at this holiday home in Smith Island. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Smith Island and Tylerton County Dock are located ...
9.6/10 Exceptional! (10 reviews)
"Great stay, Christopher was accommodating. Great place for 2-3 people. Golf cart was a great add on. Friendly neighbors. Very short walk from boat ( use green boat) Otis"
Reviewed on 28 Jul 2025
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Ewell, MD
Stay at this cottage in Smith Island. Enjoy laundry facilities, an in-room coffee maker and air conditioning. Popular attractions Smith Island and Tylerton County ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Smith Island
Commune with nature and explore the great outdoors at Smith Island during your travels in Smith Island. Discover the sunsets in this relaxing area or seek out the fishing spots.
Horse Hammock
Commune with nature and explore the great outdoors at Horse Hammock during your travels in Smith Island.
Tylerton County Dock
Explore the waterfront in Tylerton with a trip to Tylerton County Dock.