ms bookings or calendly

Microsoft Bookings vs. Calendly: Which is the Best Scheduling Software?

In today’s fast-paced world, effective time management is crucial, especially when it comes to scheduling meetings and appointments. Calendar management and appointment scheduling software has become a must have in the modern workplace, allowing customers and co-workers to schedule with each other with ease, without the back and forth. There are many different choices for appointment scheduling software, while Calendly is specifically created to fill this need, Microsoft 365 has an included piece of software – Microsoft Bookings which is a great choice as well. Let’s compare these two pieces of software and see which one fits your needs.

Microsoft Bookings: Overview

Microsoft Bookings, a part of the Microsoft 365 suite, offers a comprehensive solution for businesses that need to schedule appointments. Its integration with Microsoft Teams and the broader Microsoft environment, including Microsoft apps like Outlook, makes it a go-to choice for those already invested in the Microsoft ecosystem. Microsoft Bookings is not just a scheduling tool; it’s a complete system that allows you to manage bookings, client meetings, and staff schedules. With its robust features, it caters well to small businesses and larger enterprises alike.

Key Features

Pros and Cons


  • Deep integration with Microsoft products
  • Ideal for businesses using Microsoft Office
  • Comes included with many Microsoft 365 plans


  • Limited features, made specifically for those within the Microsoft 365 ecosystem
  • Slightly more complex interface with a slight learning curve

Calendly: The Scheduling Simplifier

Calendly, on the other hand, focuses on simplicity and efficiency. This scheduling app stands out for its ease of use, many added features and its ability to integrate with multiple platforms, not just Microsoft products. It’s a versatile tool that simplifies the process of scheduling meetings, allowing for easy setting of preferred meeting times and automatic syncing with calendars like Google Calendar and Microsoft Outlook.

Key Features

  • Easy integration with Google Calendar, Microsoft Outlook, and other platforms
  • Simple and intuitive interface
  • Free plan available with basic scheduling features
  • Option to automate text messages and email reminders

Pros and Cons


  • User-friendly with minimal setup required
  • Versatile, supporting a range of calendar systems
  • Free version available for basic needs


  • Paid versions required for more advanced features
  • If you’re already using Microsoft 365, Calendly is one more piece of software to learn

Feature Comparison

When comparing Microsoft Bookings and Calendly, it’s essential to consider specific features such as the ability to schedule appointments, manage events, send out meeting reminders, and customize the booking page.

1. Customization and Control: Microsoft Bookings offers extensive customization options, giving users full control over their scheduling pages and booking processes. Calendly is both more customizable and provides a more streamlined, user-friendly experience.

2. Integration Capabilities: Calendly wins in terms of integration with multiple platforms, making it a more flexible choice for users who operate outside the Microsoft environment. Microsoft Bookings, however, provides deeper integration within its own ecosystem. If you’re using Microsoft 365 already, Bookings is a no brainer, however Calendly wins in any other scenario.

3. Ease of Use: Calendly’s simple, intuitive interface is easier for beginners, whereas Microsoft Bookings might have a slight learning curve, especially for those not familiar with Microsoft apps.

4. Pricing: Both offer free versions, but their paid versions differ in terms of features and pricing. Calendly’s free plan is free to all, where Bookings requires a Microsoft 365 subscription.

Which One Should You Choose?

The choice between Microsoft Bookings vs Calendly largely depends on your specific needs and existing tech stack. If you’re already using Microsoft products and need advanced features like managing staff schedules or integrating with Microsoft Teams, Microsoft Bookings is your best bet.

However, if you prioritize ease of use, flexibility, and don’t require extensive integration with Microsoft apps, Calendly is the way to go. Its user-friendly interface and versatility make it ideal for individuals and small businesses looking for an efficient scheduling software without the bells and whistles.

Scheduling Tool Pricing Comparison

Calendly and Microsoft Bookings are both priced at affordable rates making the choice even more difficult. Each service offers distinct features and pricing structures. Calendly provides a straightforward pricing model with three subscription plans: Free, Standard ($10/seat/month), and Pro ($16/seat/month). The Free plan covers basic scheduling needs, while the Premium and Pro plans offer advanced features such as group events, integrations with third-party apps, and personalized branding. Calendly has an enterprise plan as well for larger businesses and additional custom requirements. Calendly’s pricing is relatively transparent, allowing users to choose a plan that aligns with their specific requirements simply by going to their pricing page.

On the other hand, Microsoft Bookings is part of the Microsoft 365 suite, catering to users seeking an integrated solution with other productivity tools. Microsoft Bookings doesn’t have a standalone pricing structure; instead, it’s bundled within most Microsoft 365 plans. This can be advantageous for businesses already utilizing Microsoft 365, as they can access scheduling features without an additional cost. However, for users solely in need of scheduling functionality, Calendly’s standalone pricing model may be more cost-effective and easier to manage. If you are interested in Microsoft Bookings and are already using Microsoft 365 or else are moving to M365, Bookings is a great option. Microsoft Bookings is included in the following M365 plans:

  • Office 365: A3, A5, E1, E3, E5, F1, F3, G1, G3, and G5
  • Microsoft 365: A3, A5, E1, E3, E5, F1, F3, Business Basic, Business Standard, Business Premium


In the debate of Microsoft Bookings vs Calendly, there’s no clear winner. Each scheduling tool has its strengths and caters to different user needs. While Microsoft Bookings is a robust, feature-rich option for those embedded in the Microsoft ecosystem, Calendly offers simplicity, flexibility and features for a wider range of users. Ultimately, the right scheduling software for you will depend on your specific requirements, be it for scheduling appointments, managing events, or automating the meeting scheduling process.

Both tools are excellent in their own right, and the best choice depends on your unique scheduling needs and existing software environment. Whether you’re a small business owner or part of a larger organization, both Microsoft Bookings and Calendly offer valuable solutions to streamline your scheduling process and save time.