
Smith Island Vacations
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- Plan, book, travel with confidence
- Better togetherSave up to ¥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Find the Best Smith Island Vacation Packages
Smith Island Hotel Deals

Pet-Friendly Smith Island Cottage w/ Golf Cart!
Ewell MD
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
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
Fully refundable
The price is ¥31,498 per night from Dec 7 to Dec 8
¥31,498
¥50,165 total
Dec 7 - Dec 8
includes taxes & fees
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.
Stay near popular Smith Island attractions
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
