Deal Island Vacations from $634

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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.

The Latest Deal Island vacation packages

Price found within the past 48 hours. Click for updated prices.
The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
Price was $692, price is now $634 per person
$634
per person
Dec 26 - Dec 29
found 11 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
8.6/10 Excellent! (1,080 reviews)
Clean, spacious room, Great Location

Reviewed on Nov 2, 2025

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $2,195, price is now $1,795 per person
$1,795
per person
Dec 26 - Dec 29
found 11 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
7.6/10 Good! (89 reviews)
Everything was exactly what you would expect for a budget friendly room, only complaint was that the steps and porch going to 3rd floor was sketchy and theres a large soft spot on 3rd floor side landing

Reviewed on Oct 17, 2025

Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,155, price is now $1,006 per person
$1,006
per person
Dec 26 - Dec 29
found 11 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
9.4/10 Exceptional! (15 reviews)
Stayed in unit 505 and it was beautiful! We loved it!

Reviewed on Aug 23, 2025

Club Ocean Villas II

Club Ocean Villas II

3.5 out of 5
North Ocean City
Price was $836, price is now $747 per person
$747
per person
Dec 26 - Dec 29
found 11 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
8.6/10 Excellent! (58 reviews)
Did not like the outdated furniture, small televisions and the hot tub wasn’t sanitized until the next day. Notified office told them hot tub cover was not on and they said they were waiting for a new cover to come in. Pools don’t open until 10 There were ants on the counter tops and the first night we were locked out . Staff said they had us listed as checked out . We did get new cards immediately. We have stayed in the condos for over 30 years Disappointed especially for paying g what we paid

Reviewed on Jul 7, 2025

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $788, price is now $714 per person
$714
per person
Dec 26 - Dec 29
found 11 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
9/10 Wonderful! (3,258 reviews)
Room was roomy and comfortable

Reviewed on Nov 3, 2025

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Deal Island Hotel Deals

Deal Island Bay Cottage

Deal Island Bay Cottage

Deal Island
$248 nightly
The price is $263 total per night from Nov 6 to Nov 7
$263 total
Nov 6 - Nov 7
Total with taxes and fees
9.6/10 Exceptional! (52 reviews)
Great Stay!
We got every year and stay here, it’s great!

Reviewed on Oct 30, 2024

Deal Island Bay Cottage
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

3 out of 5
Deal Island
10/10 Exceptional! (2 reviews)
The most well stocked property we've ever stayed! everything from extra phone chargers to blankets, tons of games and the kitchen as well.

Reviewed on Jul 7, 2025

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Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
Quaint Island Getaway

Quaint Island Getaway

Deal Island Historic District
Always a pleasure!
Staying at the Quaint Island Getaway is always a pleasure! Sarah is an accessible host, the property is cozy and clean. My party loved the new firepit.

Reviewed on Sep 24, 2024

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Quaint Island Getaway
See all 112 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.

Find the Best Deal Island Vacation Packages

Deal Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Salisbury - Ocean City Wicomico Regional Airport (SBY)
Population
470
Top Sights
Cedar Hill Marina, Shark Fin Shoal and Lower Hooper Island

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Frequently asked questions

How much does a Deal Island vacation package cost?
You can grab a vacation package to this top destination from $634 on Expedia. However, how much your vacation to Deal Island costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Deal Island?
If you'd like to score a cheap Deal Island vacation package, consider traveling in November, December and January. You'll typically find better prices on flights and hotels during these months — ideal for travelers wishing to save money.
How many days is enough for Deal Island?
The ideal length of your Deal Island vacation depends on what you'd like to see. Usually, a few days to a week will give you time to go to all the main attractions and discover some hidden spots along the way.
How to find the best Deal Island package deals?
Begin your search for a Deal Island package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Deal Island package deal right away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Deal Island getaway off to a flying start.
Is it cheaper to book a Deal Island vacation as a package?
You can enjoy significant savings on your Deal Island getaway by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Deal Island?
If you've got your Deal Island vacation dates confirmed, book as early as you can to bag some incredible deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for impromptu escapes.
Does Expedia offer Book Now, Pay Later Deal Island vacation packages?
Secure your dream escape to Deal Island with our Book Now, Pay Later vacations. No need to save like crazy or wait for the next payday — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans mean you can split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snap up bargains before they disappear.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.