Smith Island Vacation Packages

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

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Smith Island Hotel Deals

Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Smith Island MD
9.6/10 Exceptional! (49 reviews)
"Very lovely house and the host Elli is excellent."

Reviewed on Jul 6, 2026

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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 MD
10/10 Exceptional! (22 reviews)
"Just a really nice little place and we loved it! Clean, convenient, and it had everything we need! We will come back!"

Reviewed on Jun 21, 2026

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Pet-Friendly Smith Island Cottage w/ Golf Cart!
Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Smith Island MD
The price is CA $319 per night from Jul 13 to Jul 14
CA $319
CA $505 total
Jul 13 - Jul 14
includes taxes & fees
9.8/10 Exceptional! (15 reviews)
"Excellent property, excellent host. This is a very well-appointed property located very close to the ferry dock. Golf cart, bikes, and kayaks were in great shape. Chris could not have been a more responsive or helpful host."

Reviewed on Oct 28, 2025

Summer is here on Smith Island! Come out and enjoy a great season on the Bay
See all 201 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Smith Island attractions

Smith Island

9.0/10 (21 reviews)
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.
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Frequently asked questions

How much does a Smith Island vacation package cost?
You can snap up a vacation package to this top destination on Expedia. But how much your vacation to Smith Island costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Smith Island?
Travel in the low season and you're likely to get cheap Smith Island vacation packages. Remember that school vacation periods and local events and festivals can have an impact on prices, so do your research before booking.
How many days is enough for Smith Island?
The ideal length for your Smith Island vacation depends on what you'd like to see and do. Generally, a few days to a week will give you time to visit all the leading attractions and explore some hidden spots along the way.
How to find the best Smith Island package deals?
Finding a cheap Smith Island package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget, apply some filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Smith Island package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Smith Island vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Smith Island vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Smith Island?
If you're planning a spontaneous Smith Island adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Smith Island?

  1. Choose your dates: The things you plan to do in Smith Island and your preferred season can help you decide when to travel.
  2. Plan your budget wisely: In addition to the price of your stay, you should consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that could arise during your trip to Smith Island.
  3. Work out your trip length: Consider how much time you'd like to spend discovering Smith Island. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Smith Island vacation package that brings all your bookings together.

Explore a world of travel with Expedia

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