Smith Island Vacations from $780
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The Latest Smith Island Vacation Packages
- Grand Hotel Ocean City Oceanfront
Aug 29 - Sep 1Grand Hotel Ocean City Oceanfront + Flight
Downtown Ocean City3 nights3.0 star property9.0/10 - Wonderful (3,682 reviews)"We’ve stayed here more than once , that says it all"Reviewed July 17, 2026Roundtrip • Boston (BOS) - Salisbury (SBY)BOS - SBY • 1 stop SBY - BOS • 1 stop$971$780found 9 hours agoper traveler - Ocean 1 Hotel and Suites
Sep 30 - Oct 3Ocean 1 Hotel and Suites + Flight
Downtown Ocean City3 nights2.0 star property8.2/10 - Very Good (753 reviews)"The younger girl at the front desk was very helpful and friendly. It was to be welcomed by someone so pleasant and friendly. The ocean front rooms are spacious with nice balconies overlooking the boardwalk and the beach."Reviewed July 16, 2026Roundtrip • Philadelphia (PHL) - Salisbury (SBY)TTN - SBY • 1 stop SBY - TTN • 1 stop$1,085$838found 5 hours agoper traveler - Princess Bayside Beach Hotel
Aug 22 - Aug 26Princess Bayside Beach Hotel + Flight
Midtown Ocean City4 nights2.5 star property8.2/10 - Very Good (1,008 reviews)"A breakfast buffet would have been nice. Otherwise all went well"Reviewed July 17, 2026Roundtrip • New York (JFK) - Salisbury (SBY)JFK - SBY • 1 stop SBY - JFK • 2 stops$1,477$1,162found 1 day agoper traveler - Days Inn by Wyndham Salisbury
Aug 22 - Aug 26Days Inn by Wyndham Salisbury + Flight
Salisbury4 nights2.0 star property4.8/10 - (352 reviews)"Disgusting room; holes in wall, smelled like smoke, exposed unsafe outlet, stain on floor, greasy fingerprints on microwave and fridge"Reviewed July 16, 2026Roundtrip • New York (JFK) - Salisbury (SBY)JFK - SBY • 1 stop SBY - JFK • 2 stops$1,247$989found 1 day agoper traveler - Best Western Salisbury Plaza
Aug 22 - Aug 26Best Western Salisbury Plaza + Flight
Salisbury4 nights2.5 star property6.4/10 - (971 reviews)Roundtrip • New York (JFK) - Salisbury (SBY)JFK - SBY • 1 stop SBY - JFK • 2 stops$1,317$1,053found 1 day agoper traveler
Discover the most popular places to visit in Smith Island
Smith Island Hotel Deals
Pet-friendly Smith Island Cottage w/ Golf Cart!
Pet-friendly Smith Island Cottage w/ Golf Cart!
Kingsbay Mansion & Vacation Houses
Kingsbay Mansion & Vacation Houses
Rodeway Inn at Somers Cove Marina
Rodeway Inn at Somers Cove Marina
Swanendele Inn at St. Mary's Maryland
Swanendele Inn at St. Mary's MarylandFrequently Asked Questions
How much does a Smith Island vacation package cost?
Offering excellent value package deals from $780 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.