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 ...
9.6/10 Exceptional! (42 reviews)
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 ..."
Reviewed on 27 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! (15 reviews)
Amazing
"My sister and I have always wanted to visit Smith Island. This house was perfect! Well appointed, comfortable, great location and terrific host. The golf cart was such a huge bonus. We had amazing water tours, walked, relaxed, spotted more birds than we could count. Everyone on the island was beyond ..."
Reviewed on 4 Jul 2025
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Smith Island
Stay at this cottage in Smith Island. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Smith Island and Tylerton County Dock are located ...
9.8/10 Exceptional! (17 reviews)
"House was as defined but the host was very protective of her property. Also felt she was expecting us to follow her suggestions for transportation. Also, in description of property it should mention that shoes are not allowed in the house."
Reviewed on 19 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 ...
9.6/10 Exceptional! (42 reviews)
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 ..."
Reviewed on 27 Jul 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! (15 reviews)
Amazing
"My sister and I have always wanted to visit Smith Island. This house was perfect! Well appointed, comfortable, great location and terrific host. The golf cart was such a huge bonus. We had amazing water tours, walked, relaxed, spotted more birds than we could count. Everyone on the island was beyond ..."
Reviewed on 4 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.
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.