Deal Island Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Deal Island Vacation

With a vacation package to Deal Island, say goodbye to endless planning and hello to stress-free adventure. Every detail of your journey has been taken care of before you go, so you can spend more time experiencing this fantastic city. If sightseeing is on your to-do list during your trip to Deal Island, schedule a stop at top attractions such as Shark Fin Shoal. Check out Expedia's extensive range of travel options and start organizing your ultimate vacation to Deal Island now.

Top Deal Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Harrington Welcome Inn

Harrington Welcome Inn

2.5 out of 5
Price was CA $930, price is now CA $802 per person
CA $802
per person
Sep 17 - Sep 19
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
7.6/10 Good! (193 reviews)

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Midtown Ocean City
Price was CA $3,575, price is now CA $3,129 per person
CA $3,129
per person
Oct 9 - Oct 16
found 11 hours ago
Roundtrip flight included
Edmonton (YEG) to Salisbury (SBY)
8.2/10 Very good! (46 reviews)
Check in was flawless, and the room was perfect.

Reviewed on Jul 19, 2026

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was CA $3,037, price is now CA $2,685 per person
CA $2,685
per person
Oct 9 - Oct 16
found 11 hours ago
Roundtrip flight included
Edmonton (YEG) to Salisbury (SBY)
9.4/10 Exceptional! (802 reviews)
This is our fourth year staying here and we have loved our visit each time. It did seem this year that there may have been some staffing shortages as certain amenities were closed at different times than they should have been, but otherwise everything was great. Thank you again for a great week!

Reviewed on Jul 31, 2026

Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
Price was CA $2,776, price is now CA $2,467 per person
CA $2,467
per person
Oct 16 - Oct 23
found 11 hours ago
Roundtrip flight included
Edmonton (YEG) to Salisbury (SBY)
7.8/10 Good! (40 reviews)
For what I paid it wasn’t worth it. I should get money back. Some of the blinds were broken and the one bedroom window didn’t have one at all. Told the manager but no one came to install one. Nothing like the picture. Our full bed the frame was broken. The can opener should be thrown away filthy. The cleaning staff was very accommodating though. Don’t STAY THERE .

Reviewed on Jul 22, 2026

Governor's Bed and Breakfast

Governor's Bed and Breakfast

3 out of 5
Price was CA $935, price is now CA $841 per person
CA $841
per person
Sep 17 - Sep 19
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
9.6/10 Exceptional! (67 reviews)
The house was in a great location and the breakfast was wonderful.

Reviewed on Jul 25, 2026

Ready to book your vacation to Deal Island?

 

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Deal Island Hotel Deals

Waterfront Maryland Retreat w/ Dock & Bay View!

Waterfront Maryland Retreat w/ Dock & Bay View!

Deal Island Historic District MD
9.8/10 Exceptional! (10 reviews)
Great bayfront house
"This was a perfect place to stay, a bit far from our daily destination of Assateague but worth the drive for a place to unload and I unwind and relax without worrying about disturbing anyone, and with enough space for the whole family. We took advantage of the dock for crabbing and watching the sunset. ..."

Reviewed on Jul 26, 2025

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Waterfront Maryland Retreat w/ Dock & Bay View!
Saltwater Serenity Waterfront Cottage

Saltwater Serenity Waterfront Cottage

Deal Island Historic District MD
Get rates
Saltwater Serenity Waterfront Cottage
Deal Island Bay Cottage

Deal Island Bay Cottage

Deal Island MD
The price is CA $223 per night from Aug 27 to Aug 28
CA $223
CA $394 total
Aug 27 - Aug 28
includes taxes & fees
9.6/10 Exceptional! (60 reviews)
"We loved this place! We were in town for baseball. It is very nice and has all the comforts of home. Kitchen big and well equipped, house was clean and very well furnished. Nice bathrooms and a lovely screened in back porch. It is very near a beautiful beach on the bay that has some of the most beautiful ..."

Reviewed on Jun 29, 2026

Deal Island Bay Cottage
See all 124 properties in Deal 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Deal Island attractions

Crab Island

Commune with nature and explore the great outdoors at Crab Island during your travels in Deal Island. Discover the sunsets in this relaxing area.
See properties

Frequently asked questions

How much does a Deal Island vacation package cost?
Offering excellent value package deals from CA $802 on Expedia, you'll be surprised at how little a vacation to Deal Island costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Deal Island?
January, February and November are great times to search for cheap Deal Island vacation packages. Travelling in quieter periods means you can usually find better prices on accommodations and flights.
How many days is enough for Deal Island?
With a well-organized itinerary, you can easily tick off the top Deal Island sights in a few days. But if you'd like to discover hidden spots or go on day trips, think about booking your Deal Island vacation for longer.
How to find the best Deal Island package deals?
Use Expedia's filters to help you find some tempting Deal Island package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Deal Island package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Deal Island vacation as a package?
You can enjoy significant savings on your Deal Island retreat by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Deal Island?
If you've got your Deal Island travel dates confirmed, book as soon as you can to snap up some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Deal Island?

  1. Choose your dates: The things you plan to do in Deal Island and your preferred season will help you decide when to go.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and meals to flights and experiences. Your accommodations will likely be the largest expense during your trip to Deal Island.
  3. Decide how long to go away for: Now that you're up to speed on Deal Island, you can figure out the right length of your break. Create a draft itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Deal 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.