A suspension bridge over a river with autumn foliage and distant hills.

Highland Holidays from AU$4,526

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Your Highland Holiday

Lock in a Highland holiday package and get set to experience everything this city has to offer. Think about staying in the neighbourhood of Poughkeepsie Waterfront, which is good for history, families and culture. A trip to Highland is an ideal opportunity to do some sightseeing. Be sure to visit well-known attractions like Walkway Over the Hudson State Historic Park, Franklin D Roosevelt Library & Museum and Apple Greens Golf Course. Whatever your travel plans or budget, putting together the ultimate tailored Highland holiday is a walk in the park with Expedia.

The Latest Highland holiday deals

Price found within the past 48 hours. Click for updated prices.
  • 17 Dec - 23 Dec

    Hotel Seville Nomad, in the Unbound Collection by Hyatt + Flight

    Manhattan
    6 nights
    4.5 star property
    8.8/10 - Excellent (1,577 reviews)
    "We loved everything about our experience! We will stay here in the future!"
    Reviewed November 14, 2026
    Return • Melbourne (MEL) - New York (JFK)
    MEL - LGA • 2 stops LGA - MEL • 2 stops
    AU$5,795
    AU$4,526
    per traveller
    found 1 day ago
    Hotel Seville Nomad, in the Unbound Collection by Hyatt
  • 17 Dec - 23 Dec

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    6 nights
    4.0 star property
    9.2/10 - Wonderful (4,162 reviews)
    "The bar cafe in the lobby was amazing! Quick check in, clean property and very spacious rooms for this price point in NYC"
    Reviewed November 13, 2026
    Return • Melbourne (MEL) - New York (JFK)
    MEL - LGA • 2 stops LGA - MEL • 2 stops
    AU$8,355
    AU$6,085
    per traveller
    found 1 day ago
    Hotel Riu Plaza Manhattan Times Square
  • 17 Dec - 23 Dec

    Hotel Riu Plaza New York Times Square + Flight

    Manhattan
    6 nights
    4.0 star property
    9.0/10 - Wonderful (3,462 reviews)
    Return • Melbourne (MEL) - New York (JFK)
    MEL - LGA • 2 stops LGA - MEL • 2 stops
    AU$7,845
    AU$5,807
    per traveller
    found 1 day ago
    Hotel Riu Plaza New York Times Square
  • 28 Dec - 2 Jan

    The William Hotel Midtown, New York + Flight

    Manhattan
    5 nights
    3.5 star property
    9.4/10 - Exceptional (305 reviews)
    Return • Sydney (SYD) - New York (JFK)
    SYD - JFK • 1 stop JFK - SYD • 1 stop
    AU$6,912
    AU$5,149
    per traveller
    found 1 day ago
    The William Hotel Midtown, New York
  • 17 Dec - 23 Dec

    Margaritaville Resort Times Square + Flight

    Manhattan
    6 nights
    4.0 star property
    9.0/10 - Wonderful (4,134 reviews)
    "Great location and check in was simple. Walkable to lots and Times Square. Restaurants and bars are great but cannot charge to your room so that was a pain if you want to do that. Check out was the only issue. Check out was at 12 and we decided to get breakfast first. Got back to room aroud 11:40 and room key no longer worked. They shut it off. Had to go do lobby and wait in line to get it turned back on which was a bit stressful. Others had the same thing happen to them so I would watch out for..."
    Reviewed November 13, 2026
    Return • Melbourne (MEL) - New York (JFK)
    MEL - LGA • 2 stops LGA - MEL • 2 stops
    AU$6,410
    AU$4,994
    per traveller
    found 1 day ago
    Margaritaville Resort Times Square

Discover the most popular places to visit in Highland

Highland 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 Highland holiday package cost?

You can snap up a holiday package to this destination from AU$4,526 on Expedia. However, how much your holiday to Highland costs will depend on factors like your hotel choice, length of stay and season.

What are the cheapest months to go to Highland?

If you're looking to snag a cheap Highland holiday package, consider visiting in January, February and March. You'll typically find better rates on airfares and hotels during these months — perfect for a budget-friendly break.

How many days is enough for Highland?

Usually, a handful of days is enough to tick off the major attractions during your Highland holiday. But if you want to have more time to rest or take day trips, consider extending your trip.

Is it worth booking a holiday package to Highland?

Highland has everything you need for an awesome getaway — mountain biking, watersports and views are just the start. Whether you want to check out attractions such as Berean Park Beach and Franny Reese State Park, or take the path less traveled, you'll have plenty to explore on your Highland holiday.

How to find the best Highland package deals?

Bagging a cheap Highland package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Highland package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.

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

Expedia holiday packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalised Highland holiday by choosing your favourite type of stay, airline and car class.

When to book a holiday package to Highland?

If you have your Highland travel dates locked in, book as early as you can to score some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are great for impromptu escapes.

How to plan a trip to Highland?

  1. Choose when to get away: Check your schedule and get packing. Your preferred season and the type of activities available will also help you decide when to holiday in Highland.
  2. Plan your budget wisely: In addition to the price of your accommodation, you should consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Highland.
  3. Decide how long to go away for: Now that you're more familiar with Highland, you can figure out the right length of your break. Put together a draft itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a personalised Highland holiday package.

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