Chance Vacations

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  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

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    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

Find the Best Chance Vacation Packages

Chance 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 26 July 2025

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

Deal Island Bay Cottage

Deal Island MD
The price is SARĀ 597 per night from Aug 2 to Aug 3
SARĀ 597
SARĀ 1,051 total
2 Aug - 3 Aug
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 29 June 2026

Deal Island Bay Cottage
Reel Relaxation-Waterfront 3-bedroom house in Deal Island Historic District

Reel Relaxation-Waterfront 3-bedroom house in Deal Island Historic District

Deal Island Historic District MD
10/10 Exceptional! (2 reviews)
"I've been a vrbo rentee for 10 years and have rented different waterfront houses and so far this house was the best in terms of the ff:-The layout of the is excellent. If this was my house, I would design it same way.-dock is close enough but could have been bigger but it's ok also the way it is.-3 ..."

Reviewed on 11 July 2026

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Reel Relaxation-Waterfront 3-bedroom house in Deal Island Historic District
See all 99 properties in Chance
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 Chance vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Chance costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chance?
You can typically find reduced prices and greater availability in January, February and November. Take a look at our cheap Chance vacation packages and you could score some great off-season discounts.
How to find the best Chance package deals?
Use Expedia's handy filters to find some great Chance package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Chance package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Chance vacation as a package?
You can enjoy significant savings on your Chance break by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chance?
If you're planning a spontaneous Chance vacation, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Chance?

  1. Pick your travel dates: What you'd like to do in Chance and your preferred season can help you decide when to go.
  2. Figure out your budget: Ensure you have enough money to cover everything from dining out and transportation to activities and flights. Your hotel will likely be the largest expense during your trip to Chance.
  3. Decide your trip length: Think about how much time you'd like to spend discovering Chance. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Chance vacation package that brings all your bookings together.