Deal Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

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.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was CA $1,467, price is now CA $1,285 per person
CA $1,285
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Salisbury (SBY)
9/10 Wonderful! (3,964 reviews)

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was CA $1,580, price is now CA $1,363 per person
CA $1,363
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Salisbury (SBY)
9.4/10 Exceptional! (874 reviews)

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Price was CA $1,648, price is now CA $1,491 per person
CA $1,491
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Salisbury (SBY)
8.8/10 Excellent! (2,859 reviews)

Saint Tropez

Saint Tropez

3 out of 5
North Ocean City
Price was CA $1,885, price is now CA $1,714 per person
CA $1,714
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Salisbury (SBY)
9.2/10 Wonderful! (160 reviews)
My family loves booking St Tropez. Quite area with Ocean waves and beautiful sunrises. Very peaceful

Reviewed on Oct 24, 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
9.6/10 Exceptional! (14 reviews)
"We had a great time in this beautiful home. The views are truly unmatched!"

Reviewed on Sep 8, 2026

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Waterfront Maryland Retreat w/ Dock & Bay View!
Deal Island Bay Cottage

Deal Island Bay Cottage

Deal Island MD
Fully refundable
The price is CA $195 per night from Nov 2 to Nov 3
CA $195
CA $346 total
Nov 2 - Nov 3
includes taxes & fees
9.6/10 Exceptional! (62 reviews)
"nice clean place had everything we needed and the host was very responsive to any questions I had"

Reviewed on Sep 20, 2026

Deal Island Bay Cottage
1 Mi to Boat Ramp: Peaceful Deal Island Home!

1 Mi to Boat Ramp: Peaceful Deal Island Home!

Deal Island Historic District MD
6/10 (1 review)
ok
"Bath tub barely drained. ankle deep water during shower. Prefer that host use vrbo site to communicate and not text or call my cell directly. Pool was nice"

Reviewed on Jul 6, 2025

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1 Mi to Boat Ramp: Peaceful Deal Island Home!
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
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Family Vacations
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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 $1,285 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.