Smith Island, MD
Travel Guide
Visit Smith Island
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Ewell MD
Stay at this cottage in Smith Island. Enjoy laundry facilities, an in-room coffeemaker, and air conditioning. Popular attractions Smith Island and Tylerton County ...
10/10 Exceptional! (23 reviews)
"Very nice place, clean and comfortable."
Reviewed on Aug 16, 2026
Historic home on Smith Island w/ dock!
Smith Island MD
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! (54 reviews)
"We were very happy to stay at the Pearl. It was very cute and comfortable. We found everything satisfactory. We would definitely stay there again."
Reviewed on Oct 7, 2026
Come out and enjoy Autumn at the HH Ranch on Smith Island.
Smith Island MD
$275 nightly
The price is $305 total per night from Nov 9 to Nov 10
$305 total
Nov 9 - Nov 10
Total with taxes and 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 ...
9.8/10 Exceptional! (17 reviews)
"Chris was very responsive and the house was lovely."
Reviewed on Oct 14, 2026
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.
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Ewell MD
Stay at this cottage in Smith Island. Enjoy laundry facilities, an in-room coffeemaker, and air conditioning. Popular attractions Smith Island and Tylerton County ...
10/10 Exceptional! (23 reviews)
"Very nice place, clean and comfortable."
Reviewed on Aug 16, 2026
Historic home on Smith Island w/ dock!
Smith Island MD
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! (54 reviews)
"We were very happy to stay at the Pearl. It was very cute and comfortable. We found everything satisfactory. We would definitely stay there again."
Reviewed on Oct 7, 2026
Come out and enjoy Autumn at the HH Ranch on Smith Island.
Smith Island MD
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 ...
9.8/10 Exceptional! (17 reviews)
"Chris was very responsive and the house was lovely."
Reviewed on Oct 14, 2026
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.
