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An in-depth comparison between Microsoft Bookings and Calendly

As a business, do you feel as if you need extra help to plan out and manage your time? If the answer is yes, you will be pleased to know that there are many options on the market. You will find that two of the most popular calendar apps on the market are Microsoft Bookings and Calendly so it can often be tricky to decide which one to choose.  Just to state this from the start, some Microsoft 365 (formerly Office 365) licenses allow you to add Microsoft Bookings for FREE! 

In our latest blog article, we will compare both Microsoft Bookings and Calendly. 

Before we delve into the two let’s start by discussing exactly what each one does. 

Microsoft Bookings is brilliant at helping your business to save time. Put simply, it is a scheduling tool that is part of Microsoft Office which allows customers to book appointments with your business. You will find that Bookings is web-based and automatically syncs with your Outlook. Therefore, every time an appointment is made it goes straight into your customer’s calendar so the chances of people not showing up are slim.  

Calendly on the other hand is a scheduling software that prevents back and forth email chains. By adding rules, you can suggest which times are suitable for you to meet. Therefore, when clients get a link from you, they can look for a time that works best for them.  

How do the main features of both Microsoft Bookings and Calendly compare? 

Within Microsoft Bookings, you can schedule services and assign your internal team to deliver a service. The good thing about Bookings is the fact that it can read everyone’s Outlook calendar’s free/busy times, when a customer picks a service, therefore Bookings can determine which member of your team will be able to take the session. If calendars are kept up to date, the administration of this process should be minimal. Furthermore, when a customer looks to book a meeting time with yourself or a member of your team, the system will identify the gaps in your schedule that are available. From an internal perspective, the information for the meeting will be added to the diary as well as the global Bookings diary. From an external perspective, the customer will get an invitation to the meeting sent to them automatically. 

When it comes to the free version of Calendly, it enables you to schedule unlimited events that can seamlessly integrate with both Zoom, GoToMeeting and even Microsoft Teams. However, the main issue is that unless you are on a paid version, you will be unable to access customer support or have access to multiple calendars in one account. 

How do the ongoing costs of Microsoft Bookings and Calendly compare? 

Microsoft Bookings 


Free on a number of Microsoft Office 365 licenses 

Pro versions start from £6.40 per user per month 

The following is included: 

  • Multiple customer services 

  • Staff allocation to services 

  • Online Booking 

  • Calendar Sync 

  • Appointment Notifications 

  • Register of booked clients 

  • Mobile Accessibility 

  • Export of bookings 

The following is included: 

  • Appointment Notifications 

  • Calendar Sync 

  • Automatic Scheduling 

  • Client Database 

  • Online Booking 

  • Recurring Appointments 


Which of the above options is right for your business? 

It goes without saying but both Microsoft Bookings and Calendly are very similar in what they do. However, if you are already using Office 365 in your business, why would you pay for an extra service when you already have an alternative already and better still for FREE? 

It is important to note that you can make rapid improvements to Bookings through the use of Power Automate. To give you an example of this, if you have a Microsoft Booking come through, it can be synced up with Dynamics 365 Sales. 

If you do your research, you may see that some websites show that Calendly has much more functionality within it when compared to Microsoft Bookings. However, if you have Bookings along with a Microsoft Office Business License, there are other tools that are available to give you the same functionality as is built in Calendly, such as Microsoft Outlook for emails.  

You will find that Microsoft 365 has many different additions such as Microsoft Bookings that can help you to plan out your time. Why not discuss the options that are available for your business by giving one of our IT experts a call today

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