How to time your holiday booking to grab the biggest holiday deals

Information verified correct on October 27th, 2016

Whether you’re hunting for early bird specials or last minute holiday deals, here’s how to secure that cheap holiday. So you can be that much closer to booking your next one.

When it comes to holidays, you’re likely to be either a ‘planned and organised to the very minute’ person, or a ‘I’ll figure it out when I get there’ person. Is one better than the other in terms of saving money and guaranteeing yourself a cheap, yet successful, holiday?

The answer is, not really. Depending on when you’re going, and what you’re doing, whether you book early or late, you can still grab a deal. You just need to know how to look for one, and when to jump on it to make your money go the distance.

Of course, if hitting the refresh button constantly waiting for the price to drop or the sales to start stresses you out, then go right ahead and plan as early as possible to give you peace of mind. We’re all about making sure you sleep well at night.

However, for those who can live without know where you’ll be staying or what you’ll be doing in two, three, or four months time, here’s our guide for when and how to book your cheap holiday.

Booking your flight


Before booking your flight, you should consider a few important things.

  • Do you have a set destination in mind? Or are you happy to go anywhere so long as it’s away from here?
  • Do you have set dates in mind? Or are you flexible?

All these questions will help determine when you should book your trip.

When to book early:

  • If you have a set destination

then look up when its peak periods are. If you’re visiting during the peak period (namely, school and public holidays), then you should book early. Getting in as early as a year can save you heaps as there’s a tendency in Australia for prices to increase incrementally as the dates draw near. While specials may still come up in between, it’s likely they won’t for your dates as demand is high, and the higher the demand, the higher the price will be as seats fill up.

When to book later:

  • If you have a destination, but no set dates

then you can afford to sit and wait for specials. Some online travel agencies have an option to remember your destination preferences and will email you when a deals relating to it come up. Alternatively, add yourself to your favourite airlines’ mailing lists, and let their newsletters and member deals inspire you.

  • If you don’t have a set destination

  • then you can browse for specials. If you don’t have dates in mind, this is even better as you can explore who’s doing specials and when. Online travel websites like Expedia and have a ‘deals’ section to tell you what’s cheap right now. Look out for all t’s and c’s to get an idea of when the sale or deal will end so you don’t miss out.

  • If you’re really flexible with dates

  • it’ll be easier for you to grab a bargain. The best dates to fly for cheap airfares are either mid-week (Tuesday or Wednesday) or mid-weekend (Saturday night, Sunday), and generally early morning flights are cheaper than day flights. Prices always peak on Fridays for weekend holiday makers not looking to dig into their leave, so if you’re not one of them, fly during the week for a cheaper deal. Flying on major public holidays can also be a bargain, cheap flights can usually be found on Christmas Day and New Years Day.

  • If you’re extremely flexible

    , and feel like taking a last minute getaway (or don’t care if you do or don’t) then take a look at where you can go tomorrow or the day after on your travel agents’ last minute page. If there are seats that need to be filled, air carriers will drop their prices dramatically one or two days before the flight, to sell them.

  • Booking your accommodation


    Organising your accommodation early can work in your favour, but then again, so can a last minute walk in.

    When to book early:

    • If you’re visiting a country a during peak holiday period, and know how long you’ll be staying

    then book your room asap. Prices will hike up with increased demand.

    Booking early can also mean you’ll cash in on hotel specials. Hotels prefer to sell their beds as early as possible, as it means they are guaranteed to be making money out of the room. They will often do this by offering specials like ‘stay two nights, get one night free’ deals for early bookers. Many hotel websites have a dedicated ‘specials’ section of deals and packages. Take a look at them early, and look out for those niggling 'ts & cs' for what dates the deals are valid for and when the promotion period ends, and buy early to grab a bargain.

    When to book late:

    • If you really don’t mind where you stay

    then be aware that hotels with rooms still available tonight/tomorrow night often drop their prices or offer specials to fill them. So booking the day before you leave can mean a nice discount. Often, hotels that are affiliated with tour packages hold a certain amount of rooms for these customers. If the tours don’t sell out, those rooms remain vacant, and may be offered at a cut of the price during the tour dates.

    When not to even bother booking:

    • Feeling brave?

    Fly without securing accommodation, and you could be in luck. When you arrive, grab a brochure from the airport of the city’s hotels, and walk up to the counter of one and ask if they have any rooms for the night. Sounds risky, but if they do, they can knock the price down by up to half, or upgrade your room for the standard room price.

    Did you know?

    Thanks to new promotion engines like Wynbox, whether you book early or late, your chances are still the same for nabbing a bargain. Wynbox is touted to be a gamechanger on the market, providing a gamification element that gives holidaymakers the chance to win their stay. When booking, the program will tell you what your chances of winning of winning are (e.g. 1 in 5), and if lady luck’s on your side, you could score yourself free accommodation.

    Booking your tours


    Now you might be the kind of person who doesn’t book tours, preferring to discover the city at your own pace. Those who are pressed for time, or would prefer someone else take care of the organising, have the option for tours. And again, how much you save can depend on when you book.

    When to book early:

    • When you see early bird specials

    go for it. Tour companies often have early bird specials, as they’d prefer to sell out a tour, than have to pay out of their pockets for fixed costs like tour guides and bus drivers. To sell these spots they’ll either give you early bird specials, or allow you to book with a minimum deposit, and slowly pay the rest as the date draws nearer. If you know where you will be on certain dates, and you like the sound of the tour, and especially if it is peak season, then book your spot early.

    When to book late:

    • If you can help it, book your tour late.

      Up to eight weeks leading up to departure, if there are still spaces available, tours will drop their prices to sell them. Many operators have contractual agreements with hotels and air carriers, and have paid for reserved seats and rooms in advance. Rather than lose out, these tour companies drop their prices to fulfil reservations. The big catch to booking last minute tours is that you have to pay for them in full asap instead of paying in increments. But the bargain could be worth it.

    When not to book at all:

    • If you’re undecided, you don’t need to book straight away.

      Hotels and hostels often have tour desks or at least a tour company that they have contacts with who can organise a trip to see the city or its outskirts for the following day, or if you get up really early, that very day. You won’t save any money by doing this, but if you land only to realise perhaps you should have booked tour to see something, know that it’s never too late.

    Did you know?

    If you’re lucky, you may even get the tour for free if someone who has paid has cancelled at the last minute and is unable to obtain a refund, the company may be kind enough to offer up the spot. This is why you should always make friends with your tour desk operator.

    Booking your transfers and internal transport


    Trains, planes, buses, shuttles, and taxis. These are a few important things to plan when travelling.

    When to book early:

    • Internal travels are actually one of the best places you can save money on by getting in on the action, early. Pre-booking a taxi or shuttle from the airport can save you heaps. In some countries, you can pre-book your taxi and organise the price before you land, meaning if you hit traffic, all you pay is what you’ve agreed on. Do your research for this one to find out if there are taxi companies or policies in the country you’re visiting that will do this.

      Shuttles are a similar story. You can pre-book your seat and pre-pay for your transfer. This guarantees you a seat on the bus and can be cheaper than if you pay the driver when you get on the bus.

      Certain intercity trains and buses have special passes or early bird savings, while others will penalise you for late booking. Do your research to see how the intercity networks charge in your destination and book early if this is the case.

    When to book late:

    • If you really don’t know where you’ll be and when, then your best bet is to purchase last minute or at the ticket office before you hop onto your transport. Maybe you’ll pay more, but this way you won’t make unnecessary bookings that you may have to forgo if plans change.

      Another thing to keep an eye out for in your research is whether prices changes between countries. Some companies charge more if you purchase tickets from their foreign website, so it may be in your best interests to land first and buy later.

    Organising your visa early


    While we’re on the topic of things you should do early, and things you hold off until the last, one of the worst things you can do is leave your visa to the last minute. While some countries allow you to purchase a visa upon arrival, others require you to make a formal application with the consulate in your country.

    If you’re pressed for time, you can fast track your visa (at a cost), but if you wish to save on time and worry, you should purchase your visa with ample time for processing. Check the visa website for which countries require a visa (FYI if you’re off to the World Cup, Brazil is one, though Peru is not) and for information on how to obtain one.

    If you require a visa:

    • You should pre-plan your accommodation:

    Many visas require you to include an address of where you’ll be staying while on holiday. If you’re the kind to drop into the country and choose a hotel from there, or make a last-minute rush hotel purchase, this is not going to work in your favour and leaving this section blank on your visa application will mean it’ll be denied.

  • You should pre-buy travel insurance:

    Many visas also require you to provide proof that you have valid travel insurance for the length of your stay. This information should be provided to you when you apply, so make sure you purchase insurance prior to submitting your visa application or it may be denied. Don’t rush into this, as you’ll still want the right cover for you. Make an informed decision with our travel insurance finder.

  • If you don’t require a visa:

    • You can leave travel insurance to the last minute:

    Travel insurance has been made super easy by the internet. Once you’ve researched the best policy for you, it’s all comes down to purchasing it and printing out a copy for your records.

    Wherever wanderlust takes you, always do your homework and don't be afraid to add yourself onto some (or more than some) mailing lists so you can cash in on deals as they come your way. Plan what you need to (hint: visas and travel insurance) but, never be afraid to play the waiting game. Sometimes the most spontaneous or last-minute decisions can mean the freebie err- trip of a lifetime.

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