How I book a holiday cheaply – The Ultimate Guide

Last Updated on 12 April 2021 by Dan

Hello everyone! Here at the Financial Wilderness, we also have a bit of a love affair with the real Wilderness – getting out there and exploring the world with a holiday. I had planned to write this some months ago but then y’know – the world went a little bit crazy. However, given a holiday is now something we’re starting to think about again so I thought it might be time to unleash this guide…..

A holiday is just good for the soul. There’s nothing I love more than the thrill of exploring a place, finding out about the culture and history of a place and most importantly of all for me – the food!

Now a holiday is great, but it’s often not the cheapest of things in the world. As a money site, we want to make sure you can squeeze the absolute most of your holiday for the least amount of pennies.

I’ve had some tremendous success with my approach here – a particular moment of pride was managing to arrange an equivalent trip for £1,500 less than the best quote I’d got from an agent for the holiday (without making any significant modifications or compromises in terms of quality).

Why holiday research is worth it

Now I don’t want to scare you but I go quite in depth here and this is probably me at my most geeky. When you start reading this you may think “Ok, this looks like a lot of work” or “doing all that would spoil the holiday for me” I want to reassure you in a couple of ways.

I usually spend probably between 4-8 hours researching a holiday once I’ve decided where I want to go. Now some will instantly recoil in sheer horror at that figure, but I’d point to the £1,000+ saved above. That’s working out as over £100 an hour in “payment”, a much better rate than my and most non-footballers job will pay! Now I don’t always save quite this much, but I do consistently get gains that make the time worth it and get the most out of my holiday as a result.

Regardless, you can still make significant savings only doing part of this guide if you want a shorter version. I recommend doing the hotel cost reduction section of the guide, which can save you very significant wedge of cash with putting only about 15-30 minutes in.

So – onward.

The Guide

Now this guide does assume you know where you want to go in terms of your holiday destination.

The question is what to start with. If you’re flying short-haul, the accommodation is going to make up the majority of your costs so you should definitely start there. In the case of long haul it may be more even and worth researching flights first.

Phase 1 looks at selection – making sure we’re getting the best possible cost-benefit experience for our money with the hotel/AirBnB we choose.

Phase 2 focuses more on the strategies we can undertake to reduce hotel costs once we’ve decided what we want to book.

Phase 3 looks at flights, and what we can do to reduce the costs in that area.

Phase 4 covers other common questions and considerations on holiday bookings.

Phase 1: Initial accomodation research and selection

Here we shortlist hotels or an AirBnB – just jump to the appropriate section.

1A: If you want a hotel for your holiday….

Start with the dates

I start off by plugging my destination and what would be my ideal dates into my online travel agency of choice. I do this under a “Hotel only” search.

Adjust your search settings

Then I fiddle with the settings because the default ones are a bit rubbish. I’ll go to “Accommodation Type” or whatever the equivalent is and change it to just Hotels or anything else similar that I’m interested in. The reason for this is that these sites consistently feature lots of small apartments that generally aren’t easy to independently verify (and usually have about 1 review of 5 stars so dominate searches). Doing this clears those out.

I’ll then filter by “Guest rating”. There’s a couple of things on this to note:

I’m not filtering by hotel class (the standard 2-star, 3-star, 5-star system). When you begin to research star ratings you find out they’re really not that meaningful. They’re very country specific in how they’re applied and often are quite heavily weighted towards facilities rather than service and atmosphere. I’ve had better experiences in some 2 and 3 star hotels than supposed 5 stars.

The experiences of real guests are generally more reliable (just have a read of the reviews and comments to make sure they do appear to be genuine, unfortunately a hazard of the internet).

Secondly is to make sure you site of choice does simply say “guest rating” and not something like “guest rating + our favourites”).

This is unfortunately not the same thing and something I’ve increasingly noticed as a problem with the online travel agents. What “our favourites” actually mean is that you’ll be looking at the hotels which the agent receives the best commission for rather than what are truly the best rated hotels.

We don’t want that – we’re out of the best hotel for you, not Mr. Expedia‘s wallet (who do this) so if you see it, I recommend conducting your search via another site.

Form a Shortlist

I then form a shortlist of hotels that have consistent high ratings from guests with plenty of reviews that are at a reasonable price.

A family, relaxing on holiday at the beach.

Do a crossover with Tripadvisor

For my shortlisted hotels, I’ll then search for the specific hotel on Tripadvisor to check on the reviews there. These can be more enlightening and throw up issues such as location or individual issues.

I’ll use this to pick out the one that offers the best combination of rating and price, and have a spare up my sleeve in case.

Why don’t you just use Tripadvisor to start with?

They’ve got really bad at filtering things by “Best Value” which is best commission paid to Tripadvisor, not the best hotel. Even when I’ve played with the settings there I’ve seen the odd listing that doesn’t make sense – so Tripadvisor is a backup check, not my main method of search.

1b: If you’re happy with an AirBnb for your holiday….

I do check AirBnb if I’m going to somewhere like a major city in Europe or America. I’m more reluctant to use this when off the beaten track but my experiences have been honestly excellent when using it in these locations and usually (but not always) the cheapest option as you’re getting a more basic service.

If you’re going down the AirBnB route, I recommend only booking apartments that have had multiple guests staying on previous occasions and are well reviewed. It’s worth looking at the comments as well. Some of the very cheapest may be new listings or only have 1/2 reviews, but unfortunately there are still occasional AirBnB scams out there so I take an approach of safety first.

You also need to be careful you’re in a good location. I like to find a guide to the city I’m looking to visit and identify what good and bad areas are, and where the majority of sites or locations I want to visit are.

I then put in my dates and travel find it easier to switch to a map view rather than the list view – it lets you get a great view of comparative pricing and what you’re getting in each location.

Finally if I have some flexibility in my dates I play around with date combinations as the prices can vary a surprising amount. I’ve found no hard and fast rules on what works best beyond expect seasonality/school holidays to affect pricing and weekends are slightly more expensive, but you could probably guess that yourself!

Trial and error is your friend here, and it’s worth thinking about this alongside airline costs.

There’s no much more we can do on accommodation costs with an AirBnB unless you’re a new customer (if so, if you use my signup link here you can get up to £34 off your first booking at this link here.)

Otherwise you can jump to the flights section below unless interested in my hotel moneysaving tips!

Phase 2: How to minimise hotel costs

Ok! Now we’ve chosen where we’d like to stay to get the best possible hotel, let’s reduce those costs at much as possible to get as much holiday as we can for our money.

There a couple of things to consider here.

The “pure” cost:

It’s time to compare everywhere that’s offering a room at your chosen hotel. My favourite resource for doing this is Kayak – despite being affiliated with, I’ve found that their results seem to be consistently reliable for price comparison.

What Kayak does is search all the online travel providers (and direct) to see what prices they’re quoting, and then it tells you what the best price is. By default, it will come up with the most basic and cheapest room, but if you click on the hotel name it will do the same comparison with all the different level of rooms the hotel offers.

If I have flexibility, I run this search a few times with various date combinations to find out when appears to be the cheapest time.

Reworking for the cost after cashback

Now here’s where it gets a little bit tricky….

The amount the online travel agents will give you back at TopCashback is absolutely massive relative to the cost of the purchase. (If you don’t know what Cashback is and how it works, this article explains it).

I often find Expedia in the 12-18% cashback bucket for instance. This makes a huge difference – if you’re spending £1000 on a holiday, £180 back covers a heck of a lot of spending money.

It also means the cheapest base price may not be the cheapest price you can get.

Let’s demonstrate:

Site A will charge you £1000 for your 7 night stay, and pays out a rate of 8% cashback.

Site B will charge you £1050 for your 7 night stay, a pays out a rate of 15% cashback.

With site A we’re paying effectively £920. We hand over £1000 and get £80 (the 8%) back in cashback.

Despite the fact site B is more expensive on the site, we’re effectively only paying £892.50. We hand over £1,050 and but get £157.50 (the 15%) back in cashback.

Thus, we can do better than simply the cheapest site. It does takes some time to get your head around but really does work.

So it’s worth searching the online travel agencies on TopCashBack and comparing their rates to factor this into your calculations. (I’ve always found TopCashBack has paid out the best rates of any payout site every time I’ve done a compare, which is why I recommend them).

If maths scares you and you’re concerned you “can’t do percentages” to work this out – simply take:

The cost of the room and multiply by the percentage rate of cashback. That tells you what your cashback payout should be.

You then simply do cost of room minus cashback payout to work out true cost.

An important note on cashback

Before you actually make your final purchase, close all windows on your browser and then load up only TopCashback and go directly to the site through this without Kayak, Tripadvisor or anything else up in the background.

The reason for being cautious here is that cashback will be paid out on the basis of who gets the credit for the last click through to the site – you want that to be TopCashback on your behalf. This will help stop any tracking getting confused and you missing out on your cashback.

You should also note that whilst I’ve personally never had a problem with my cashback being tracked on online travel agents, issues with tracking/clickthroughs do occasionally happen, so be cautious about the fact it’s possible that it can fail and you lose out.

If prices work out the same, who should I go with?

If all else is equal, I recommend using Hotels.Com if possible and making sure you opt in to their reward scheme as it’s the most generous of all of the online travel agents. Basically when you have stayed 10 nights in properties, you get the average value of those nights as a free nights stay.

I haven’t found anything that beats that (let me know if you have).

Beyond that, simply go with personal preference (making sure of course you book safely and somewhere with a reputation).

Why aren’t you booking the flight and hotel together to save on your holiday?

Please note that generally speaking cashback pays out much better at the online travel agents for a hotel only booking than a hotel and flight combined. Whilst there are sometimes some savings from booking them together, I haven’t found an example yet where the benefit outmatched the cashback I’d have lost.

Isn’t it better to book directly with the hotel?

It’s definitely worth checking the cost of booking directly for sure, and if it’s the cheapest option after cashback I’d always advocate booking direct.

Unfortunately I often find the base price is cheapest for booking direct, but I can’t get any cashback meaning the “true” price is effectively higher. The exception to this rule may be if you’re booking into a hotel that’s part of a chain – I have a liking for more boutique-type hotels which does make it more tricky!

The real reason people ask this question though is the worry you might receive a lower level of service at the hotel. The answer to this is not particularly clear cut – some hotels may give a slightly nicer room or a gift on arrival to those booking directly, but it’s not guaranteed.

I’ve tried both approaches, and the truth is I’ve never noticed any significant differences between the two. I take the view that I’ve never experienced anything I felt as determent or less satisfactory from booking through an online travel agent, and so would rather simply take the certainty of booking on the cheapest rate (unless the difference is pretty minimal).

What about physical or high street travel agents?

Worth checking but more miss than hit in most cases.

Various ethnic or specialist travel agencies sometimes can get some really fantastic deals where they specialise in a location.

There is the potential that the “bulk buy” or partnership deals that travel agents have with a hotel mean it’s cheaper to book through them than direct. It’s rare, but I have had it happen (via Trailfinders, who I have to say when I have used this method have been excellent).

I generally skip this step, unless I’m looking for something particularly specialised.

Phase 3: Booking a cheap flight

As we’ve shown there’s lot we can do to save extra money on a hotel booking. It’s actually quite a bit harder to save money with flights, and as a result I have only pieces of general advice here.

A holiday hammock on the beach

If you’re going long haul and booked well in advance, await the a sale from the airline and move fast.

A good example of this would be flying long haul with British Airways – they’ll have a big sale every half year or so which generally speaking has good prices if you’re got plenty of time to work with.

But book when you see it – just because something in on sale, doesn’t mean the airline stops using dynamic pricing and the cost can go up.

Apparently according to research the sweet spot is about eight weeks away on average – in my experience flight prices rarely go down on any remotely popular route.

If you’re going short haul it’s generally better to book immediately.

That price elasticity is over particularly extreme with the smaller airlines. The only time I’m playing the last-moment cheap fare game is when I have nothing booked, could leave tomorrow and know I can get a cheap room at the other side.

It’s worth comparing flight options.

It’s still worth running a comparison to see what prices you can get. Personally I really like Google Flights, although SkyScanner is probably the best known in the market.

The reason I like it is that you can easily see the prices in grid format to see how prices vary at different dates, and you can easily change the settings for timings for direct flights only etc.

It’ll also tell you what the average price for that route at that time is so you can judge if the flight is relatively expensive or cheap.

Just be aware that the flight comparison sites tend to use the very lowest prices on offer which usually doesn’t include bags (even long haul).

I haven’t yet found an algorithm site I think is worth it

There’s a couple of sites which claim to find you the cheapest time to book by analysing flight prices and telling you if you should stay or wait. I’ve tried these a couple of times now and in each case got burned by paying a higher price than if I’d just booked it immediately, hence my book now advice above.

If all else equal, go for the airline with the best loyalty scheme

The short haul carriers like Easyjet and Ryanair don’t tend to really have these, but airline loyalty schemes can really stack up over time. If you find a carrier you like it’s definitely worth targeting them and where the price difference is minimal sticking to them religiously (signing up for all schemes and flying occasionally with everyone just doesn’t get you anywhere).

An airline credit card can help you save

In the UK, British Airways and Virgin Atlantic both have credit cards which allow you to gain Avios or Air Miles pretty quickly. Just be aware that the value of using these is generally much better long haul than short haul, so it’s not worth wasting these on an economy short haul flights.

They usually also have top-notch earnings when you’re making bookings with the airlines using your card (I.E you’re buying a British Airways flight with your BA card, or a Virgin flight with your Virgin card).

You can read more about those cards on our article on rewards credit cards here.

Phase 4: Other considerations/FAQ

How can I maximise my travel money?

I wrote an article on this earlier in the year which you can find here, and believe all the advice in that is still current.

If I’m paying for anything in a foreign currency from the UK as well when making my bookings, I want to be sure I’m doing it on a card with a good FX rate.

Is there anything I can do to save money on a holiday as a solo traveller?

Sadly this is much more difficult – you find the odd hotel here and there that has a single room and therefore you can save at but it’s very much the exception not the rule.

If you are travelling alone one way to do it reasonably cost effectively is by going with G Adventures or Intrepid who run small group tours. I’ve done this several times myself with both companies when going a little more off the beaten track and found the experience superb, making some fantastic friends along the way.

As a solo traveller you’ll either simply pay the normal rate and share a room with someone of the same sex, or you can pay a small supplement to guarantee having your own room.

(You can also get lucky and find that there’s no-one you need to share with!)

In the Above you book your hotel and flight separately. Is there any dangers with that?

It can make things complicated where things go wrong. If you book both as a single with an online travel agent covered by ABTA you’ve bought a “package holiday” and it falls to that agent to sort out anything that goes wrong with those parts of your trip and where they may impact each other.

Where you book each piece individually if anything changes you’d have to make changes with each supplier, and may lose out if say, issues with flights mean you can’t make your hotel.

It’s really important to have decent insurance to cover these. Speaking of….

When should I book travel insurance for my holiday?

As soon as you book. Travel insurance is designed to cover things going wrong in the run up to the holiday, not just the days you’re actually away as many believe. If you’re taking a couple of holidays a year, I do believe having an annual travel insurance policy is a good idea.

Are you looking to go camping?

Then check out which has lots of fantastic tips and advice for you!

That’s pretty much it.

I appreciate I’ve covered a lot here! Please let me know if you have any other questions or queries and I’m very happy to add them in the FAQ section.

And if you’ve made a super saving on your own holiday, or got an additional tip of my own that I’ve missed I’d love to hear from you!

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