When Should You Book a Holiday?

Knowing when to book a holiday can make a big difference to the price you pay — but there isn’t one perfect time that works for every trip.

The best time to book depends on where you’re going, when you want to travel and how flexible you can be.

If you’re tied to school holidays or travelling during a popular period, booking earlier can give you much more choice. If your dates and destination are flexible, waiting for a deal can sometimes work in your favour.

Here’s how I approach it.

Book Early for Peak Travel Periods

If you’re travelling during school holidays or another high-demand period, I generally recommend starting your search early.

This includes:

• Summer 2026 holidays – Explore deals
• October 2026 half-term – Explore deals
• Christmas 2026 holidays – Explore deals
• New Year 2027 holidays – Explore deals
• Easter 2027 holidays – Explore deals
• Summer 2027 holidays – Explore deals

Booking earlier doesn’t guarantee you’ll get the lowest price, but it usually gives you a better choice of hotels, rooms, flight times and departure airports before availability becomes more limited.

This is particularly important for families who need specific dates and don’t have the flexibility to travel a week earlier or later.

Plan Ahead for Long-Haul Holidays

For destinations such as Thailand, Bali, Dubai, Mexico, the USA and the Caribbean, I prefer to start researching several months ahead.

Long-haul trips often involve more decisions — flights, hotels, transfers and sometimes internal travel — so starting early gives you time to compare everything properly.

You don’t necessarily need to book the moment flights become available. Start watching prices, research your accommodation and get an idea of what represents good value for your dates.

Then you’re in a much better position to recognise a deal when you see one.

When Can Last-Minute Holidays Be Worth It?

Last-minute holidays can still offer great value, but they’re much better suited to travellers who can be flexible.

They can be worth exploring if:

• You’re open to several destinations
• You can travel at short notice
• You can use different departure airports
• Your dates can move by a few days
• You’re not restricted to school holidays
• You’re flexible about the hotel

The more specific your requirements are, the riskier it becomes to wait.

If you need a particular destination, hotel, room type and exact travel dates, I’d be much less inclined to rely on finding a last-minute bargain.

Is There a Best Day to Book a Holiday?

There’s no magic Tuesday, Wednesday or Sunday when holidays suddenly become cheapest.

Flight and holiday prices can change constantly depending on availability, demand and numerous other factors.

What’s often more useful is being flexible with your travel dates.

Flying a day earlier or later, changing the length of your trip or considering another departure airport can sometimes make a noticeable difference to the overall price.

So rather than waiting for a particular day of the week to press “book”, concentrate on comparing the dates and options available to you.

Don’t Wait Forever for the Price to Drop

It’s tempting to find a holiday you love and keep checking it in the hope that it becomes cheaper.

Sometimes it will.

Sometimes the price will increase — or the hotel, room or flights you wanted will disappear.

That’s why I don’t think holiday planning should become a game of trying to predict the absolute lowest possible price.

If you’ve compared your options, the holiday suits you and you’re comfortable with the price, sometimes that’s the right time to book.

Compare Before You Book

I always recommend checking more than one place before committing.

Useful websites include:

• Skyscanner
• Icelolly
• Expedia
• Trip.com
• On the Beach
• Jet2holidays
• HolidayPirates

You don’t need to spend hours comparing every travel website available. Check a few relevant options and make sure you’re comparing the final holiday price and what’s included, rather than the headline price alone.

So, How Far in Advance Should You Book?

There’s no single number of months that works for every holiday.

My general approach is:

Peak dates or school holidays: start looking early because choice matters.

Long-haul holidays: start researching several months ahead so you have time to compare flights, accommodation and the overall trip.

Flexible off-peak trips: you have more freedom to watch prices or consider last-minute deals.

Very specific hotel, destination or dates: don’t rely on a last-minute deal appearing.

The less flexible you are, the more benefit there is in planning ahead.

Final Thoughts

So, when should you book a holiday?

For school holidays, summer travel, Christmas and other high-demand periods, I’d generally start planning early. For flexible, off-peak travel, you have more freedom to watch prices and take advantage of deals when they appear.

Most importantly, don’t become obsessed with trying to book at the mythical “perfect” moment.

Compare a few providers, understand what your holiday should realistically cost and book when you find an option that suits your budget, dates and travel plans.

You might occasionally see it cheaper afterwards — that’s travel pricing.

What matters is that you found a holiday you wanted at a price you were happy to pay.

Looking for your next adventure?

Explore hand-picked holiday deals, honest hotel reviews, practical travel guides and destination inspiration from around the world. Whether you’re dreaming of Thailand, a European escape or somewhere completely new, discover more ideas to inspire your next trip.