Deal Island Vacations from $896

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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.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $1,059, price is now $896 per person
$896
per person
Jan 9 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Salisbury (SBY)
8.8/10 Excellent! (1,008 reviews)
The room was spotless. The staff were courteous and helpful. Fantastic hotel!

Reviewed on Oct 28, 2025

Marvel's on the Creek

Marvel's on the Creek

4 out of 5
Price was $1,645, price is now $1,399 per person
$1,399
per person
Dec 8 - Dec 11
found 23 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
10/10 Exceptional! (159 reviews)
The property was unique because the room we had was called the Honeymoon Suite. It had an entire kitchen plus a master suite with separate shower and an old fashioned four legged tub. Plus we had a private balcony and a separate entrance to come and go. Our scene each morning that we woke up to was a river with a pier where my husband fished. Ms. Debbie was pleasant, sweet and a perfect host who welcomed us with open arms. We will definitely be back. Thank you for a beautiful time.😊

Reviewed on Jul 8, 2025

Cambridge Inn

Cambridge Inn

2 out of 5
Price was $1,457, price is now $1,244 per person
$1,244
per person
Dec 8 - Dec 11
found 23 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
5.2/10 (536 reviews)
The motel looked to be recently updated, and was clean and neat. Parking was convenient. Staff was friendly and helpful.

Reviewed on Oct 5, 2025

St Michaels Inn

St Michaels Inn

2.5 out of 5
Price was $1,501, price is now $1,285 per person
$1,285
per person
Dec 8 - Dec 11
found 22 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
8.2/10 Very Good! (1,000 reviews)
Frustrating that even with plenty of vacant rooms they stack everyone side by side for efficiency sake, the walls are thin and noise is an issue, easily avoidable but when I called to suggest they spread people out just a bit if they have the opportunity I was responded to quite rudely, dismissed really. Decided to cancel an upcoming reservation unfortunately. Used to feel like a great value.

Reviewed on Oct 28, 2025

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 out of 5
Price was $1,476, price is now $1,265 per person
$1,265
per person
Dec 8 - Dec 11
found 23 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
9.2/10 Wonderful! (906 reviews)
The staff was very helpful and friendly. Breakfast was great.

Reviewed on Oct 31, 2025

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Deal Island Hotel Deals

Deal Island Bay Cottage

Deal Island Bay Cottage

Deal Island
$143 nightly
The price is $263 total per night from Nov 5 to Nov 6
$263 total
Nov 5 - Nov 6
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 $896 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.