Sherwood Holidays from AU$3,689

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The Latest Sherwood holiday deals

Price found within the past 48 hours. Click for updated prices.
  • 28 Dec - 3 Jan

    The Godfrey Hotel Chicago + Flight

    Downtown Chicago
    6 nights
    4.5 star property
    8.8/10 - Excellent (2,608 reviews)
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$4,440
    AU$3,689
    per traveller
    found 8 hours ago
    The Godfrey Hotel Chicago
  • 28 Dec - 3 Jan

    The Peninsula Chicago + Flight

    Downtown Chicago
    6 nights
    5.0 star property
    9.8/10 - Exceptional (1,012 reviews)
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$7,537
    AU$5,906
    per traveller
    found 8 hours ago
    The Peninsula Chicago
  • 28 Dec - 3 Jan

    Swissotel - Chicago + Flight

    Downtown Chicago
    6 nights
    4.5 star property
    9.0/10 - Wonderful (3,578 reviews)
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$4,711
    AU$3,890
    per traveller
    found 8 hours ago
    Swissotel - Chicago
  • 28 Dec - 3 Jan

    Arlo Chicago + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.4/10 - Exceptional (2,443 reviews)
    "Great."
    Reviewed November 10, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$4,555
    AU$3,774
    per traveller
    found 8 hours ago
    Arlo Chicago
  • 28 Dec - 3 Jan

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    6 nights
    4.5 star property
    9.4/10 - Exceptional (199 reviews)
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$4,447
    AU$3,695
    per traveller
    found 8 hours ago
    The Talbott, Autograph Collection

Sherwood 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 Sherwood holiday package cost?

Offering excellent value package deals from AU$3,689 on Expedia, you'll be surprised at how little a holiday to Sherwood costs! Our packages mean less travel planning for you and greater savings.

What are the cheapest months to go to Sherwood?

January, February and September are the best times to search for cheap Sherwood holiday packages. Travelling in less busy periods means you can usually find better prices on flights and hotels.

How many days is enough for Sherwood?

The ideal duration for your Sherwood holiday depends on what you'd like to do and see. Usually, a few days to a week will give you time to hit all the top attractions and explore some hidden treasures along the way.

How to find the best Sherwood package deals?

Use Expedia's filter tool to find some fabulous Sherwood package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Sherwood package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your holiday package as soon as possible.

Is it cheaper to book a Sherwood holiday as a package?

An Expedia holiday package could score you significant savings when compared to booking accommodation and flights individually. Better still, you can personalise your Sherwood getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.

When to book a holiday package to Sherwood?

If you have your Sherwood holiday dates locked in, book as soon as you can to snap up some outstanding deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for impromptu escapes.

How to plan a trip to Sherwood?

  1. Choose when to get away: Check your schedule and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to visit Sherwood.
  2. Set a budget: Consider expenses such as transportation, flights and meals when working out how much to put aside for your trip to Sherwood. Then, select a hotel that matches your budget, whether that's an affordable stay or a lavish getaway.
  3. Decide how long to go away for: Now that you know more about Sherwood, you can figure out the perfect length of your holiday. Create a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your airfare and accommodation: Once you've nailed down your dates and duration, lock in the ideal Sherwood holiday package for you.

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