Smith Island Vacations from $621

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The Latest Smith Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

2.5 out of 5
Midtown Ocean City
Price was $704, price is now $621 per person
$621
per person
Dec 3 - Dec 7
found 10 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Salisbury (SBY)
8.8/10 Excellent! (1,001 reviews)
Nice place and great breakfast options that’s included

Reviewed on Sep 20, 2025

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Midtown Ocean City
Price was $1,014, price is now $856 per person
$856
per person
Dec 3 - Dec 7
found 10 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Salisbury (SBY)
8.2/10 Very Good! (38 reviews)
I loved the dock and the gorgeous sunsets .

Reviewed on Sep 7, 2025

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Price was $808, price is now $703 per person
$703
per person
Dec 3 - Dec 7
found 10 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Salisbury (SBY)
8.6/10 Excellent! (2,156 reviews)
Great beach view, really nice rooms, I would stay again.

Reviewed on Oct 12, 2025

Cypress River Inn & Spa

Cypress River Inn & Spa

5 out of 5
Price was $1,100, price is now $960 per person
$960
per person
Dec 3 - Dec 7
found 10 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Salisbury (SBY)
No reviews
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $1,149, price is now $1,004 per person
$1,004
per person
Dec 3 - Dec 7
found 10 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Salisbury (SBY)
8.8/10 Excellent! (1,005 reviews)
Hyatt regency is more like a Hyatt place … fewer people working , in room dining is in paper boxes with plastic cutlery , but still regency pricing . But excellent pet policy and everyone so kind to pets

Reviewed on Oct 3, 2025

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Discover the most popular places to visit in Smith Island

Smith Island

Commune with nature and explore the great outdoors at Smith Island during your travels in Smith Island. Discover the sunsets in this relaxing area, or seek out the fishing spots.

Smith Island

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
$326 nightly
The price is $346 total per night from Oct 14 to Oct 15
$346 total
Oct 14 - Oct 15
Total with taxes and fees
9.6/10 Exceptional! (13 reviews)
"This was our first visit to Smith Island and the Double H was perfect. It was close to the ferry landing so getting there was very easy. The house was well appointed and felt like home as soon as we arrived. We enjoyed the quiet of the island and we were able to fully disconnect and relax Thank you ..."

Reviewed on Oct 7, 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
9.6/10 Exceptional! (45 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

Get rates
Historic home on Smith Island w/ dock!
Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

Smith Island
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

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Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island
See all 192 properties in Smith Island
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.

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 $621 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.