Smith Island Holidays

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Smith Island Holiday

Our pick of the best Smith Island Hotel Deals

Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Smith Island
9.4/10 Exceptional! (43 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

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

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Ewell
9.8/10 Exceptional! (16 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

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Pet-Friendly Smith Island Cottage w/ Golf Cart!
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

Smith Island
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

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IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
See all 185 properties in 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.

Discover the most popular places to visit in Smith Island

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.

Smith Island

Frequently asked questions

How much does a Smith Island holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday 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 holiday 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 holiday as a package?
Expedia holiday 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 customised Smith Island holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday 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 holiday 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.