Deal Island Holidays

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Top hotels in Deal Island

Waterfront Maryland Retreat w/ Dock & Bay View!

Waterfront Maryland Retreat w/ Dock & Bay View!

Deal Island Historic District
9.8/10 Exceptional! (7 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 26 Jul 2025

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Waterfront Maryland Retreat w/ Dock & Bay View!
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 24 Sep 2024

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

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

2 out of 5
Deal Island Historic District
10/10 Exceptional! (4 reviews)
"My family and I had an amazing time here. The home was beautiful with lots of indoor and outdoor space. Kitchen was equipped with everything you needed. Wi-Fi access was easy with the information that was given. Host were great. Thank you for the great memories."

Reviewed on 12 Aug 2025

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Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
See all 111 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.

Frequently asked questions

How much does a Deal Island holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday 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?
January, February and November are great times to look for cheap Deal Island holiday packages. Opting to travel in quieter months means you can typically find reduced prices on flights and hotels.
How many days is enough for Deal Island?
With a well-organised travel plan, you can easily tick off the top Deal Island attractions in a few days. But if you prefer to discover hidden gems or go on day trips, consider booking your Deal Island holiday for longer.
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 holiday as a package?
You can enjoy significant savings on your Deal Island getaway by booking a customised holiday 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 holiday package to Deal Island?
If you've got your Deal Island holiday 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.
How to plan a trip to Deal Island?

  1. Choose when to get away: Check your schedule and get your bags packed. Your favourite time of year and the activities on offer will also help you decide when to holiday in Deal Island.
  2. Calculate your budget: Make sure you have enough money to pay for everything from dining out and transportation to activities and airfares. Your hotel will probably be the biggest expense during your trip to Deal Island.
  3. Decide how long to go away for: Now that you know more about Deal Island, you can figure out the perfect length of your break. Create a rough plan and allocate enough time to get through everything on your must-do list.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Deal Island holiday 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.