Smith Island Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 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
Top hotels in Smith Island
Historic home on Smith Island w/ dock!
Smith Island MD
€283
8 Sept - 9 Sept
includes taxes & fees
9.6/10 Exceptional! (52 reviews)
"The owner, Chris, was very helpful with what we needed to bring, which was so helpful. Would definitely recommend. House was clean and well stocked."
Reviewed on 2 Aug 2026
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 21 Jun 2026
Summer is here on Smith Island! Come out and enjoy a great season on the Bay
Smith Island MD
€315
17 Aug - 18 Aug
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 28 Oct 2025
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
Smith Island
9.0/10 (21 reviews)
Step back in time on Maryland's only inhabited offshore island, where watermen's traditions thrive. Sample the famous Smith Island cake while exploring quaint villages surrounded by Chesapeake Bay views.
Horse Hammock
Horse Hammock is an uninhabited island in Maryland's Chesapeake Bay, offering pristine natural landscapes for wildlife enthusiasts. Access requires private boat transport, making it a secluded birdwatching retreat.
Tylerton County Dock
Explore the waterfront in Tylerton with a trip to Tylerton County Dock.
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?
- Choose your dates: What you'd like to do in Smith Island and your preferred season can help you decide when to go.
- 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.
- 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.
- 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.
