Shirley Vacations from $395

Book a Hotel + Flight or Car together to unlock savings

The Latest Shirley Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Sep 4 - Sep 7

    Comfort Inn at Thousand Hills + Flight

    Foggy River Woods
    3 nights
    2.5 star property
    9.0/10 - Wonderful (841 reviews)
    "Nice and clean room and the hotel was clean as well. Love staying there it was peaceful as well."
    Reviewed July 27, 2026
    Roundtrip Chicago (CHI) - Springfield (SGF)
    ORD - SGFNonstop SGF - ORDNonstop
    $553
    $395
    per traveler
    found 1 day ago
    Comfort Inn at Thousand Hills
  • Sep 4 - Sep 7

    Roark Creek Resort + Flight

    Downtown Branson
    3 nights
    4.5 star property
    9.0/10 - Wonderful (4 reviews)
    "The check-in was a pain because there is no office on site. I had to contact someone by phone and get instructions on how to enter my room. Other than that, the room was great."
    Reviewed July 21, 2026
    Roundtrip Chicago (CHI) - Springfield (SGF)
    ORD - SGFNonstop SGF - ORDNonstop
    Save 100% on your flight
    $1,108
    $761
    per traveler
    found 1 day ago
    Roark Creek Resort
  • Aug 26 - Aug 31

    The Suites at Fall Creek + Flight

    Fall Creek
    5 nights
    3.0 star property
    8.6/10 - Excellent (1,753 reviews)
    "Would stay again"
    Reviewed July 27, 2026
    Roundtrip Denver (DEN) - Springfield (SGF)
    DEN - SGFNonstop SGF - DENNonstop
    $557
    $420
    per traveler
    found 1 day ago
    The Suites at Fall Creek
  • Sep 4 - Sep 7

    Hyatt Vacation Club at The Lodges at Timber Ridge, Branson + Flight

    Skyview
    3 nights
    4.0 star property
    9.2/10 - Wonderful (1,153 reviews)
    Roundtrip Chicago (CHI) - Springfield (SGF)
    ORD - SGFNonstop SGF - ORDNonstop
    $640
    $488
    per traveler
    found 1 day ago
    Hyatt Vacation Club at The Lodges at Timber Ridge, Branson
  • Sep 30 - Oct 3

    Landing Apartments near Lakes of Forest Hill + Flight

    Cordova
    3 nights
    4.0 star property
    Roundtrip Chicago (CHI) - Memphis (MEM)
    ORD - MEMNonstop MEM - ORDNonstop
    Save 100% on your flight
    $924
    $711
    per traveler
    found 1 day ago
    Landing Apartments near Lakes of Forest Hill

Shirley Hotel Deals

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 Shirley vacation package cost?

You'll find cheap prices from $395 on Expedia for your Shirley break. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Shirley costs.

What are the cheapest months to go to Shirley?

You're likely to find lower prices and greater availability in January, February and November. Browse our cheap Shirley vacation packages and you could score some great off-season discounts.

How many days is enough for Shirley?

The ideal length of your Shirley vacation depends on what you'd like to see. Typically, a handful of days to a week will give you plenty of time to hit all the major sights and discover some hidden spots along the way.

How to find the best Shirley package deals?

Begin your search for a Shirley package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Shirley package deal right away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Shirley getaway off to a flying start.

Is it cheaper to book a Shirley vacation as a package?

Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Shirley vacation by choosing your preferred accommodation type, airline and car class.

When to book a vacation package to Shirley?

If you're considering a spontaneous Shirley vacation, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find awesome deals on your flights and hotels by booking ahead.

Does Expedia offer Book Now, Pay Later Shirley vacation packages?

If you're like us, you love discovering new places but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Shirley break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.

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