Smith Island Vacations from $979
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The Latest Smith Island vacation packages
Price found within the past 48 hours. Click for updated prices.
Beach Walk
Downtown Ocean City
$1,622
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
7.8/10 Good! (114 reviews)
We would definitley stay at the Beach Walk again for a short stay, the only complaints I would have is the internet one night kept going in and out and the staff really wasnt helpful about it when my boyfriend went down the next day and the third floor balcony could use some work.
Reviewed on Aug 31, 2026
Ocean Terrace Family Apartments
Downtown Ocean City
$1,125
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Salisbury (SBY)
7/10 Good! (52 reviews)
Everything was great. But apt 2 needs a dehumidifier. The room is beginning to smell like mildew. And the mattresses were more firm than I like.
Reviewed on Aug 30, 2026
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See all available trips from Columbus to Smith Island
View all tripsStay 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.
Tylerton County Dock
Explore the waterfront in Tylerton with a trip to Tylerton County Dock.
Horse Hammock
Horse Hammock is an uninhabited island in Maryland's Chesapeake Bay, offering pristine natural landscapes for wildlife enthusiasts. Access requires private boat transportation, making it a secluded birdwatching retreat.
Smith Island Hotel Deals
Historic home on Smith Island w/ dock!
Smith Island MD
$285 nightly
$302 total
Sep 7 - Sep 8
Total with taxes and 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 Aug 2, 2026
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
Spacious 5-bedroom house with WiFi, AC and private deck on charming Smith Island
Smith Island MD
10/10 Exceptional! (1 review)
Amazing Adventure
"Amazing adventure! Peaceful! Beautiful! Privacy! Gourmet Kitchen! The house is set back from the neighborhood on a large lot. The decks are new and comfortably furnished. We cooked breakfast and dinner for 3 days and the well-equipped kitchen was perfect. Our days started and ended with gourmet meals, ..."
Reviewed on Jun 18, 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.
Find the Best Smith Island Vacation Packages
Smith Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | J. Millard Tawes Museum and Somers Cove Marina |
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Frequently asked questions
How much does a Smith Island vacation package cost?
Offering excellent value package deals from $979 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?
November, December and January are great times to look for cheap Smith Island vacation packages. Choosing to travel in less busy months means you can typically find better prices on flights and accommodations.
How many days is enough for Smith Island?
The ideal duration for your Smith Island vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you enough time to tick off all the leading sights and discover some hidden spots 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.
Does Expedia offer Book Now, Pay Later Smith Island vacation packages?
Secure your perfect trip to Smith Island with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or hold off until payday — we've teamed up with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to budget for your trip and snap up cheap deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
