Smith Island Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Smith Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Princess Royale Oceanfront Resort
North Ocean City
CA $2,420
per person
Oct 15 - Oct 17
found 13 hours ago
Roundtrip flight included
Victoria (YYJ) to Salisbury (SBY)
8.8/10 Excellent! (2,721 reviews)
Friendly courteous staff and a beautiful facility. The beachfront restaurant is really nice and the indoor pool is a pleasure every time we come.
Reviewed on Sep 11, 2026
Castle in the Sand
Midtown Ocean City
CA $2,304
per person
Oct 15 - Oct 17
found 13 hours ago
Roundtrip flight included
Victoria (YYJ) to Salisbury (SBY)
8.8/10 Excellent! (1,019 reviews)
Second time staying at this hotel, always have a good time here the staff is always friendly and accommodating. I also love the restaurant on site. They’re happy hour buy one get one is a must and the fact that it’s right on the beach is another win.
Reviewed on Sep 11, 2026
Ready to book your vacation to Smith Island?
Smith Island Hotel Deals
Historic home on Smith Island w/ dock!
Smith Island MD
9.6/10 Exceptional! (52 reviews)
"The owner, Chris, was very helpful with what we needed to bring, which was so helpful. Would definitely recommend. House was clean and well stocked."
Reviewed on Aug 2, 2026
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Ewell MD
CA $76
CA $327 total
Sep 13 - Sep 14
includes taxes & fees
10/10 Exceptional! (23 reviews)
"Very nice place, clean and comfortable."
Reviewed on Aug 16, 2026
Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart
Smith Island MD
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.
Stay near popular Smith Island attractions
Smith Island
9.0/10 (21 reviews)
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.
Tylerton County Dock
Explore the waterfront in Tylerton with a trip to Tylerton County Dock.
Horse Hammock
Commune with nature and explore the great outdoors at Horse Hammock during your travels in Smith Island.
Frequently asked questions
How much does a Smith Island vacation package cost?
You can snap up a vacation package to this top destination from CA $2,284 on Expedia. But how much your vacation to Smith Island costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Smith Island?
Travel in the low season and you're likely to get cheap Smith Island vacation packages. Remember that school vacation periods and local events and festivals can have an impact on prices, so do your research before booking.
How many days is enough for Smith Island?
The ideal length for your Smith Island vacation depends on what you'd like to see and do. Generally, a few days to a week will give you time to visit all the leading attractions and explore some hidden spots along the way.
How to find the best Smith Island package deals?
Finding a cheap Smith Island package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget, apply some filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Smith Island package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Smith Island vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Smith Island vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Smith Island?
If you're planning a spontaneous Smith Island adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Smith Island?
- Choose your dates: The things you plan to do in Smith Island and your preferred season can help you decide when to travel.
- Plan your budget wisely: In addition to the price of your stay, you should consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that could arise during your trip to Smith Island.
- Work out your trip length: Consider how much time you'd like to spend discovering Smith Island. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Smith Island vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
