Smith Island Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Smith Island

Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina

2 out of 5
700 Norris Harbor Dr, Crisfield, MD
Fully refundableReserve now, pay when you stay
The price is 2.464.957 ₫ per night from 11 Sept to 12 Sept
2.464.957 ₫
2.785.401 ₫ total
11 Sept - 12 Sept
includes taxes & fees
Rodeway Inn at Somers Cove Marina
Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland

5 out of 5
49946 Airedele Rd, Ridge, MD
9.8/10 Exceptional! (29 reviews)
"Everything about the Swanendele Inn was exceptional: the location, the accommodations, the facilities, the decor, the hosts, and, not least, the breakfast. In fact, you could spend several days just exploring the remarkable antiques and artifacts around the place. However, what made the strongest ..."

Reviewed on 4 Aug 2025

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Swanendele Inn at St. Mary's Maryland
Kingsbay Mansion & Vacation Houses

Kingsbay Mansion & Vacation Houses

3.5 out of 5
27999 Coulbourn Creek Road, Marion Station, MD
The price is 10.810.060 ₫ per night from 24 Sept to 25 Sept
10.810.060 ₫
11.999.167 ₫ total
24 Sept - 25 Sept
includes taxes & fees
"Jerry & David were wonderful hosts and made us feel welcome and comfortable. They surprised us with an incredible breakfast. We’ll be back, for sure."

Reviewed on 16 Jun 2024

Kingsbay Mansion & Vacation Houses
See all 184 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.

Frequently asked questions

How much does a Smith Island holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday 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?
The off-season is the best time to head to Smith Island if you're trying to save. Another tip for finding cheap Smith Island holiday packages? Try to avoid public holidays and any major events or festivals.
How many days is enough for Smith Island?
The ideal duration of your Smith Island holiday depends on what you'd like to see and do. Usually, a few days to a week will give you enough time to check out all the main attractions and explore some hidden gems 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 holiday as a package?
Expedia holiday 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 customised Smith Island holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday 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.
How to plan a trip to Smith Island?

  1. Choose your dates: What you'd like to do in Smith Island and your preferred season can help you decide when to go.
  2. Set a budget: Factor in expenses such as flights, meals and transportation when calculating how much to save for your trip to Smith Island. Then, select a property that suits your budget, whether that's a low-cost stay or a deluxe getaway.
  3. Decide how long to go away for: Now that you're more familiar with Smith Island, you can work out the ideal length of your break. Create a rough itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick a Smith Island holiday package that brings all your bookings together.