A person in a kayak on a calm body of water during sunset.

Smith Island Vacations from $410

Book a Hotel + Flight or Car together to unlock savings

The Latest Smith Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 30 - Jan 3

    Grand Hotel Ocean City Oceanfront + Flight

    Downtown Ocean City
    4 nights
    3.0 star property
    9.0/10 - Wonderful (4,006 reviews)
    Roundtrip • Miami (MIA) - Salisbury (SBY)
    MIA - PHL • Nonstop TTN - FLL • Nonstop
    $507
    $410
    per traveler
    found 1 day ago
    Grand Hotel Ocean City Oceanfront
  • Dec 30 - Jan 3

    Beach Front Villa in Dewey Beach + Flight

    Rehoboth by the Sea
    4 nights
    4.0 star property
    Roundtrip • Miami (MIA) - Salisbury (SBY)
    MIA - PHL • Nonstop TTN - FLL • Nonstop
    Save 100% on your flight
    $4,232
    $3,429
    per traveler
    found 1 day ago
    Beach Front Villa in Dewey Beach
  • Dec 30 - Jan 3

    Bethany Beach Ocean Suites Residence Inn by Marriott + Flight

    Downtown Bethany Beach
    4 nights
    3.0 star property
    9.0/10 - Wonderful (877 reviews)
    "Everything starting with checking in and out was excellent."
    Reviewed November 7, 2026
    Roundtrip • Miami (MIA) - Salisbury (SBY)
    MIA - PHL • Nonstop TTN - FLL • Nonstop
    $815
    $664
    per traveler
    found 1 day ago
    Bethany Beach Ocean Suites Residence Inn by Marriott
  • Dec 30 - Jan 3

    Hyatt Place Dewey Beach + Flight

    Dewey Beach
    4 nights
    3.0 star property
    8.8/10 - Excellent (1,001 reviews)
    "Beautiful hotel, staff were very friendly. Breakfast was very good. Parking garage was a little tight for bigger SUV’s."
    Reviewed November 8, 2026
    Roundtrip • Miami (MIA) - Salisbury (SBY)
    MIA - PHL • Nonstop TTN - FLL • Nonstop
    $788
    $659
    per traveler
    found 1 day ago
    Hyatt Place Dewey Beach
  • Dec 30 - Jan 3

    Dagsboro Retreat + Flight

    Dagsboro
    4 nights
    2.0 star property
    10/10 - Exceptional (1 review)
    "I loved it"
    Reviewed July 17, 2026
    Roundtrip • Miami (MIA) - Salisbury (SBY)
    MIA - PHL • Nonstop TTN - FLL • Nonstop
    $707
    $612
    per traveler
    found 1 day ago
    Dagsboro Retreat

Discover the most popular places to visit in Smith Island

Frequently Asked Questions

How much does a Smith Island vacation package cost?

Offering excellent value package deals from $410 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.