Smith Island Vacations

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Find the Best Smith Island Vacation Packages

Smith Island Hotel Deals

Pet-Friendly Smith Island Cottage w/ Golf Cart!

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

Pet-Friendly Smith Island Cottage w/ Golf Cart!
Historic home on Smith Island w/ dock!

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

Historic home on Smith Island w/ dock!
Come out and enjoy Autumn at the HH Ranch on Smith Island.

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

Come out and enjoy Autumn at the HH Ranch on Smith Island.
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

How much does a Smith Island vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation to Smith Island costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Smith Island?
The off-season is the best time to head to Smith Island if you're trying to save. Another tip for finding cheap Smith Island vacation packages? Try to avoid public holidays and any major events or festivals.
How many days is enough for Smith Island?
The ideal duration of your Smith Island vacation depends on what you'd like to see and do. Usually, a few days to a week will give you enough time to check out all the main attractions and explore some hidden gems along the way.
How to find the best Smith Island package deals?
Begin your search for a Smith Island package deal by entering your destination and travel dates under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Smith Island package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Smith Island adventure off to a flying start.
Is it cheaper to book a Smith Island vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still get the flexibility to create a customized Smith Island vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Smith Island?
Secure incredible bargains by booking your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Smith Island getaway.
How to plan a trip to Smith Island?

  1. Choose your dates: What you'd like to do in Smith Island and your preferred season can help you decide when to go.
  2. Set a budget: Factor in expenses such as flights, meals and transportation when calculating how much to save for your trip to Smith Island. Then, select a property that suits your budget, whether that's a low-cost stay or a deluxe getaway.
  3. Decide how long to go away for: Now that you're more familiar with Smith Island, you can work out the ideal length of your break. Create a rough itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick a Smith Island vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.