Smith Island
Travel Guide
Visit Smith Island
Historic home on Smith Island w/ dock!
Smith Island
Stay at this vacation 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
Stay at this cottage in Smith Island. Enjoy laundry facilities, an in-room coffeemaker, and air conditioning. Popular attractions Smith Island and Tylerton County ...
9.8/10 Exceptional! (17 reviews)
Wonderful anniversary trip
"We absolutely loved our stay on Smith island in this adorable cottage. Laura the host was very responsive, friendly and helpful. Being first timers to the island, I had several questions that were answered very quickly. The cottage was clean, well stocked (which is important for this type of unique ..."
Reviewed on 12 Aug 2025
Get away to relax on Smith Island in the Chesapeake Bay with golf cart included
Smith Island
The price is €303 per night from 25 Aug to 26 Aug
€303
25 Aug - 26 Aug
includes taxes & fees
Stay at this vacation home in Smith Island. Enjoy free WiFi, a fitness center, 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
Stay at this vacation 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
Get away to relax on Smith Island in the Chesapeake Bay with golf cart included
Smith Island
Stay at this vacation home in Smith Island. Enjoy free WiFi, a fitness center, 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
Stay at this cottage in Smith Island. Enjoy laundry facilities, an in-room coffeemaker, and air conditioning. Popular attractions Smith Island and Tylerton County ...
9.8/10 Exceptional! (17 reviews)
Wonderful anniversary trip
"We absolutely loved our stay on Smith island in this adorable cottage. Laura the host was very responsive, friendly and helpful. Being first timers to the island, I had several questions that were answered very quickly. The cottage was clean, well stocked (which is important for this type of unique ..."
Reviewed on 12 Aug 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.
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.