Choosing a Booking System

by Mia Steinberg

It’s admittedly difficult for us to give unbiased advice on finding a good booking system, as we run one—and we love our product. That being said, we will refer customers to other systems if we sense that our software won’t be a good fit. Like any good relationship, both parties need to be happy, or things generally end in tears.

Like any good relationship, both parties need to be happy, or things generally end in tears.

No matter which booking system you choose, we want to help, so we’ve compiled a short list of considerations and questions you should be asking of any potential system or piece of software. Keep these concepts in mind during your search for a booking system; it will help make the process as pain-free as possible, and hopefully guide you in the right direction.


shutterstock_183277097Unfortunately, finding a booking software that meets the needs of your business can be a tiresome process. Booking systems have a wide range of features, and almost-identical business will have very different needs.  It’s a good idea to map out what you think you’ll need beforehand, and ask lots of questions before spending too much time integrating things.

First of all, be wary of booking systems which require upfront costs to get started; you should be able to try the system before paying for it. We’ve all had the experience of paying upfront for something we then regret; sometimes you have to swallow your pride and eat the cost. But make no mistake: your booking software is a big deal for your business. Some systems claim to support every setup and business type known to man, embodying the old adage “jack of all trades, master of none.” You deserve the chance to see if something will work for you, because it will fundamentally alter the way your business runs. Take your time, read reviews, and don’t lock yourself into anything until you’re sure you’ve found a winner. That said, be realistic; it’s highly unlikely that you’ll find a 100% perfect system that addresses every last one of your issues and leaves chocolates on your pillow. In business, as in love, the name of the game is high standards tempered by pragmatic expectations.

Any booking system should include these basic features:

– A sensible inventory management system that can handle bookings (as opposed to just items for sale). You should be able to itemize every tour, rental, or accommodation you offer, and be able to adjust inventory without much fuss. You should also be able to easily add, modify, and delete items from your inventory, without erasing existing sales records. And the customer should be able to browse your site and pick their desired booking without getting confused.

– A calendar synced with the rest of your website, to help you keep track of bookings. If you’re going to offer self-service booking software on your website, you’re going to get business outside of business hours. If your booking software just takes the payment and isn’t connected to your calendar to fill in the dates, then you face a massive headache of trying to pencil in all of the bookings yourself–and isn’t that the sort of annoyance you’re trying to avoid?

– A user friendly interface. This might seem like a no-brainer, but it could make or break your business! Make sure you know exactly what your customers are going to see, and make sure it works as advertised. People don’t have a lot of patience to struggle with an interface.

Customer support. This sort of software needs to be customised to some degree, and you may run into confusion or problems. You should be able to get assistance from the company that made the program; trying to Google around to solve your problems gets old really quick.

Integrations into other tools you use. Your software shouldn’t be closed off from the rest of the internet; you should be able to use social media, review sites, and other plugins right within the system. It makes life much easier for a business that’s even partially web-based.


Let’s have a look at what options exist for managing your bookings:

Do it yourself

It’s not uncommon for us to see businesses using a combination of unrelated tools to manage bookings. This can include Google Calendar / Outlook, MS Excel, E-mail forms, Paypal Buttons and the humble sticky note. This is occasionally (lovingly) referred to as a frankenstein booking system, but that doesn’t mean it’s not an option for you.

Generally speaking, if you don’t do a whole lot of bookings, then an e-mail form on your website supported by a calendar on your backend may get the job done. If you can manage the amount of emails that come in and keep track of everything, you’re pretty much set. You generally know when this setup has stopped working for you: if overbookings are becoming a problem and e-mails / phone calls are getting overwhelming, it may be time to consider a different approach. And if your competition offers online bookings, then they may very well be getting the business that should be yours.

Pros: Cheap, easy to set up, and likely using tools that are already familiar to computer owners.

Cons: Limited features, relies on human capability, and doesn’t scale up as required to handle increased sales.

Desktop Software

There are more traditional booking systems which exist as software installed on your computer. In some cases, a client/server setup links multiple desktop clients to a central reservation system, but this connection only occurs behind the scenes: customers can’t access it remotely. Desktop systems can be a good choice in places where internet connectivity isn’t available or is unreliable; many business owners also feel more confident knowing that their software is installed directly on their hard drives, instead of mysteriously floating in the cloud. Unfortunately, desktop software can be very expensive, and you need to buy the entire program up front. With this sort of setup, the only computers that will affect your bookings are the ones you directly control; so while a server outage or hacking attack won’t faze you, a computer virus or hard drive failure could cripple your entire business and compromise vital information.

Ideally, you should make sure that your desktop booking system has some sort of integration into your website. But be warned: the combination may be clunky, if it’s offered at all, as desktop programs just can’t anticipate the near-infinite number of possible website designs, and thus will not be able to adapt as needed to your site.

Pros: No Internet connection required; not vulnerable to online issues.

Cons: High up-front costs and no customer connectivity. You need to be physically in front of the computer in order to access your records.

Build your own

Build vs buy: it’s an age-old question in software. Building your own booking system has the potential to be the best possible fit; you can design a system that meets every need of your business. On the flip side, you could end up spending more time building and operating the system than you do on your core business.  Even basic booking systems get complex quick, and feature creep can be disastrous.

With that said, if you find you are making too many compromises with potential booking systems then it may be time to roll up your sleeves and build to spec. If hiring an outside firm, make sure they understand your industry, have good communication with you, and have excellent references. Building custom software is just like building your own home; you want your contractor to be a partner in progress instead of a frustrating burden.

Pros: It’s whatever you want it to be. You own it.

Cons: Can be very expensive to build and maintain, and impossible to merge with other systems.

Cloud / Software-as-a-Service

Yes, we’re guilty of buzzword bingo. It seems these days that every website promotes themselves as “in the cloud”, to the point where it’s easy to lose track of the true meaning behind the phrase. Essentially, cloud software takes the requirements of traditional software and makes them available to you on demand. This is also known as Software-as-a-service (SaaS).

Cloud software vendors are responsible for maintaining and updating the software. New features roll out regularly—ideally at no cost — and you can access the program from any computer with an internet connection. The basic idea behind a cloud booking system is that it centralizes your data; customers can book from your website and feed into a central reservation system in real time. The entire thing can be downloaded and integrated into your website with minimal tinkering required, fitting as easily as a key into its lock–in fact, ready-to-use software like this is often called “turnkey software”.

A good cloud offering will include an open API should you wish to build onto it, and be able to integrate mobile apps, site plugins, and third party systems like Paypal or Stripe—without these, it’s simply a website within your website.

Pros: Turnkey, cost effective, and communicates with other relative services.

Cons: You don’t own the software. Limited ability to customize core features.


Selecting a service that fits with your business model is very important.  It’s probably the first item on your checklist that you should consider before heading down the path with a booking system. You could find the greatest booking system in the world, but if it doesn’t meet your budget or scale with your business, you’ll likely end up replacing it.  Look ahead to your busy season, and make sure the pricing is within your budget. Here are some of the most common pricing breakdowns for online booking software; desktop or custom-made systems are usually just bought upfront.


Commission-based pricing is a traditional model and easy one to understand: when a booking is made, you pay a percentage of proceeds to the software manufacturer. Rates can range widely from 1% to 25%.

The key question to ask here is: are you paying a revenue share to your booking system for customers that would otherwise already arrive on your website?  Moreover, are you paying a commission on repeat business? Paying commission on net new business is one thing, but paying on existing business is expensive.

User Fees

Some booking systems offload the commission or transaction fee by way of a service fee to the customer. It’s a bit like a commission in reverse: instead of the booking system taking a percentage off of your advertised price, they will instead add the fee to the customer’s final total, usually added along with applicable taxes at the end of the purchasing process.

The key point to consider here is that, whether you’re charged commission or a user fee, this is increasing the price of your service. These pricing plans don’t necessarily mean that the software is useless or should be avoided, but it’s good to find out if your competition charges a booking fee, and if customers are more likely to call you if they know there is no service fee associated with your business.

Volume Plans

Most cloud/SAAS platforms operate on a pay per use model. This means you pay based on how much you use the software, and it’s often bundled in plans which give you several options to fit your needs. Mailchimp charges per message delivered; Dropbox’s billing is dependant on how much storage you use; and Checkfront charges based on how many bookings you run through the system. With pay-per-use, your ratio of software expenses to increased business is much smaller; subscriptions can be cancelled if need be, and may therefore be cheaper than upfront software purchases in the long run. But if you don’t get the volume, you may end up paying for something you’re not using. It’s important to have an established idea of your customer volume in order to ensure your investment won’t go to waste.


Free booking software does exist.  There are open source, ad supported, and flat free systems out there.  Many of these put the responsibility of hosting and maintenance onto you, the business owner, and updates and customer support may be very bare-bones—in some cases, you will end up asking Google many of your troubleshooting questions. Be sure you have someone technical available to manage a free system, and always check to see that the software is actively maintained and securely retained by its owners. These sorts of programs can be very easy to exploit, and a security breach could spell disaster for your business.


Getting support when you need it is critical.  Self service support portals are great, but when push comes to shove, can you get the answers you need in a timely matter? What’s the turnaround for support? Are you charged extra to get answers to your questions, and is there support available in your timezone?

Other Questions to Ask

Who owns my data, and can I take it with me when I leave?

Your historical booking data and customer records are important to your business.  We’ve encountered countless customers who have had their data held hostage by a booking system—sometimes by design or policy, other times just by the fact they can’t export the data in a friendly format. It can be due to a poorly designed system that doesn’t play well with others, or a calculated way to amass your data (and potentially sell it to third parties). Make sure that you know exactly who will own the data you collect, and what the terms of the contract are in this regard.

Are there other happy customers like me?

Make sure someone else in your industry is using your potential booking system, and check to see if they are happy. Go to Google and type in the company name; does the word “scam” or “complaint” come up in the auto-suggestion list? There are hundreds of ways to find real reviews from pissed off customers; don’t become another horror story.

Can I accept payments online?

Buying and reserving things online is no longer a newfangled fad; it’s a fundamental part of everyday life. There’s nothing more frustrating than trying to book a service and being told that you must call to give your credit information, or routed to an unfamiliar payment site. Customers know which payment systems are secure, and are more likely to book if they can pay through Paypal, Stripe, or other well-trusted merchants.

Do you integrate into my website?

More and more bookings are done online. Customers want to be able to book at a time convenient to them, and filling out a form that promises you’ll get back to them soon just won’t cut it. An integrated platform looks professional, feels trustworthy, and streamlines the user experience. If the booking software can operate entirely within your website, it will become a seamless part of your overall online presence and heighten a customer’s sense of security and trust.

Do you integrate into the tools I use to run my business?

Your booking system shouldn’t be a silo. It should happily integrate into the other tools you use on a daily basis—calendars, social media profiles, mobile apps, accounting software, whatever you use. Your goal is to streamline your business by making bookings easier to create, track, and implement; if a system will force you to manually input all new bookings into your POS back end calendar, or add new customers to your email lists one by one, then it may be more trouble than it’s worth. Of course, no single piece of software is going to be perfect for everyone’s needs; here at Checkfront we get requests from our clients asking for compatibility with things we never even imagined we’d need when we launched. But tool integration is a key part of making your booking system a central, vital part of your business and website.


So what should you take away from this post? Are you feeling overwhelmed with the different varieties, pricing options, and ideal features? We know how you feel; it’s a big decision, but if made right it can totally transform your business. Our FAQ and Support sections are great resources if you have questions or want to know if Checkfront is right for you. We’re not the best thing for everyone, but we’re a great fit for most companies, and if you have questions, we want to hear them!