Smith Island Vacations from $322
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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
$2,426
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Salisbury (SBY)
7.6/10 Good! (126 reviews)
We never slept here. The room was incredibly dirty. Stained sheets, stained carpet, god only knows what on the walls in the bathroom. The table and chairs were a table that folded out from the wall with a stick underneath. The chairs were two rusty folding chairs. The blinds in the window were busted up and only covered half the window. I honestly don’t know how they’ve not been shut down. We quickly found another hotel.
Reviewed on Oct 13, 2026
Microtel Inn & Suites by Wyndham Milford
$362
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Fort Myers (RSW) to Salisbury (SBY)
8.8/10 Excellent! (832 reviews)
Perfect for an overnight stay. Rick was pleasant and provided us with an excellent option for dinner.
Reviewed on Oct 17, 2026
Boardwalk One
Downtown Ocean City
$1,092
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
7.4/10 Good! (179 reviews)
The room was fresh cleaned, hot showers and plenty of space. Staff was very nice and informative. We were able to have covered parking. We watched the major storm with the high waves and wind from balcony but didn't disturb us with doors closed. Location was great for walking boardwalk. When too wet had an excellent tv and reception in the room.
Reviewed on Sep 28, 2026
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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 transportation, making it a secluded birdwatching retreat.
Smith Island Hotel Deals
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
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
Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart
Smith Island MD
9.4/10 Exceptional! (3 reviews)
"Super clean and provided all necessary means, but food. lol"
Reviewed on Oct 11, 2026
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 $322 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.