Smith Island Vacations from $768

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The Latest Smith Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Sahara Motel
Surf Villa Apartments
Inn at Perry Cabin
Americana Motor Inn
Miramar Condominiums
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Smith Island Hotel Deals

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Smith Island MD
$275 nightly
The price is $304 total per night from Feb 12 to Feb 13
$304 total
Feb 12 - Feb 13
Total with taxes and 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 Oct 28, 2025

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Smith Island MD
9.4/10 Exceptional! (46 reviews)
We enjoyed ourselves besides the weather that turned bad, fall is not the best time to visit Smith Island, everything was operating on limited hours.

Reviewed on Oct 3, 2025

Historic home on Smith Island w/ dock!
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

Smith Island MD
9.8/10 Exceptional! (18 reviews)
The Jazzy 6 loved the accommo- dations and the kitchen was great. Stocked with seasonings, coffee and tea. Marykim was a wonderful hostess. She had our golf cart delivered to Idol Hour and our Smith Island Strawberry cake was in the refrigerator waiting for us. We loved Idol Hour and would stay again. ...

Reviewed on Aug 18, 2025

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
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 $768 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.