Smith Island Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Smith Island Vacation Packages

Smith Island Hotel Deals

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Ewell MD
10/10 Exceptional! (23 reviews)
"Very nice place, clean and comfortable."

Reviewed on 16 August 2026

Get rates
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Smith Island MD
9.6/10 Exceptional! (54 reviews)
"We were very happy to stay at the Pearl. It was very cute and comfortable. We found everything satisfactory. We would definitely stay there again."

Reviewed on 7 October 2026

Get rates
Historic home on Smith Island w/ dock!
Come out and enjoy Autumn at the HH Ranch on Smith Island.

Come out and enjoy Autumn at the HH Ranch on Smith Island.

Smith Island MD
Fully refundable
The price is AEDĀ 735 per night from Nov 30 to Dec 1
AEDĀ 735
AEDĀ 1,119 total
30 Nov - 1 Dec
includes taxes & fees
9.8/10 Exceptional! (17 reviews)
"Chris was very responsive and the house was lovely."

Reviewed on 14 October 2026

Come out and enjoy Autumn at the HH Ranch on Smith Island.
See all 200 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.

Stay near popular Smith Island attractions

Smith Island

9.0/10 (21 reviews)
Step back in time on Maryland's only inhabited offshore island, where watermen's traditions thrive. Sample the famous Smith Island cake while exploring quaint villages surrounded by Chesapeake Bay views.
See properties

Frequently asked questions

How much does a Smith Island vacation package cost?
You can snap up a vacation package to this top destination 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 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," "Traveler 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 favorite 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?

  1. Choose your dates: The things you plan to do in Smith Island and your preferred season can help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.