Wondering when to book your flights and hotels ? The answer isn’t as simple as “the earlier, the better” or “wait until the last minute.”

Book too early and you might pay more than necessary. Wait too long and prices can rise, your favourite hotel might sell out, or the flight times you want may disappear. There isn’t one magic booking window that guarantees the cheapest price.

After years of planning my own trips, I’ve found that the best approach is to start looking early, track prices and know when to stop waiting.

For me, that starts around six months before a trip. Here’s exactly how I do it.

As a general rule, I recommend starting to look around six months before your trip. This doesn’t mean you need to book everything six months in advance. Instead, use this time to understand prices and your options.

At this point, I’ll usually:

• Check flight prices and different routes
• Set up flight price alerts
• Compare hotel options
• Look for accommodation with free cancellation
• Check whether trains, tours or attractions need to be booked in advance

From there, I’ll monitor prices and decide when I’m comfortable booking. The strategy is slightly different for flights and hotels.

Flights are probably the hardest part of a trip to time. Prices can change depending on the route, airline, season and demand, so there isn’t one magic date when flights suddenly become cheaper. That’s why I prefer to start looking early and monitor prices rather than waiting for a specific booking window.

My flight strategy

I usually start looking around six months before departure. Once I’ve decided where I’m going, I’ll use Skyscanner to compare airlines, routes and prices, and I’ll set up a price alert to keep an eye on the fare. I’ve found that long-haul flights can sometimes be reasonably priced six months before a trip, but on some routes, waiting until two or three months before departure can result in a cheaper fare.

The problem?

It’s a gamble. The price might drop or it might increase significantly. Your preferred flight could also sell out, leaving you with worse flight times or fewer options. So if your dates are fixed, I wouldn’t wait until two or three months before departure purely because you hope the price will fall. If you’re flexible and happy to take the risk, you can keep monitoring. But if you’ve found a price you’re comfortable with, I’d usually book it and move on.

A useful starting point

Type of trip	When I’d start looking
Short-haul	Around 2–4 months ahead
Long-haul	Around 6 months ahead
Peak season	6–8 months ahead
Flexible dates	3–6 months ahead
Fixed annual leave	Around 6 months ahead

These are starting points rather than strict rules. The best window varies considerably by route and travel dates. If your annual leave is fixed, I’d prioritise availability and a price you’re happy with over trying to find the absolute lowest fare.

Hotels are where I use a slightly different strategy. I start looking around six months before my trip, but I don’t necessarily consider that my final booking. Instead, I’ll try to find a hotel I like with free cancellation, book it and then keep checking the price.

My hotel price-checking strategy

Let’s say I’m travelling in six months.

I’ll find a hotel I like on Booking.com and, where possible, choose a rate that allows free cancellation. I’ve then secured the room I want, but I can continue monitoring the price. If the same room becomes cheaper later, I can potentially cancel the original booking and rebook at the lower price.

This gives me the best of both worlds : Book early for choice and availability, but keep the flexibility to save later.

If you do this, make sure you’re comparing the same room, dates, number of guests and cancellation conditions, and always check the cancellation deadline before cancelling.

I’d be especially inclined to book early if you’re travelling:

• During school holidays
• Over Christmas or New Year
• During a major event
• To a particularly popular destination
• As a group
• For a specific hotel or room type

For quieter trips, you may have more flexibility. The key is to balance price, availability and flexibility, rather than simply waiting as long as possible.

I recommend researching both at the same time. Once I know my destination and dates, I’ll look at flights and accommodation together. This gives me a better idea of the overall cost and lets me spot anything unusually expensive.

When it comes to booking, it depends on the trip. If flights are expensive and your dates are fixed, I’d usually prioritise the flights. If accommodation is limited or you’ve found a hotel you really want, I’d make sure that is secured too.

My general order is:

1. Check flights
Understand prices and start tracking them.

2. Check accommodation
Shortlist hotels and compare prices.

3. Confirm your dates
Make sure everything works with your annual leave.

4. Book the flights
Once you’ve found a price you’re comfortable with.

5. Secure the hotel
Ideally with free cancellation.

6. Book anything that can sell out
Such as trains, restaurants, attractions and popular experiences.

Sometimes. But “sometimes” isn’t a strategy I’d rely on if your annual leave is limited.

Last-minute hotel deals can happen, particularly during quieter periods. But during peak travel periods, waiting can have the opposite effect as availability decreases. Flights are even harder to predict. You might get lucky and find a cheaper fare closer to departure, but you could just as easily end up paying considerably more.

If you’re completely flexible about where and when you travel, last-minute trips can work brilliantly. But if you’ve already requested your annual leave and chosen your destination, you’re taking a much bigger risk by waiting.

Personally, I’d rather monitor prices early and make an informed decision than gamble my entire trip on a last-minute deal.

You don’t need to know the exact cheapest day to book. You just need a system.

Here’s mine:

The exact timeline will change depending on the destination and trip, but the principle stays the same: Start early. Track prices. Stay flexible where you can. Then book when you’re happy.

There is no magic day to book a flight or hotel. My approach is to start looking around six months ahead, monitor prices and use flexibility wherever possible.

For hotels, that means looking for free cancellation and continuing to check the price. For flights, it means using price alerts and deciding when a fare is good enough to stop waiting.

Because ultimately, the cheapest possible price isn’t always the best deal especially when your annual leave is limited. The right flight, the right hotel and the right dates are often worth more than chasing the absolute lowest price.

Book when you’re happy with the combination of price, choice and flexibility then stop checking and start looking forward to your trip.