The business world is changing rapidly, as are the ways of doing things. The way that businesses operate has changed dramatically over the past few years, with more companies moving to a remote working model.

In the past, it was common for people to manage their own bookings, and countless hours were spent on spreadsheets and emails. Nowadays, there’s an abundance of online booking platforms available, which make managing your schedule much easier than ever before.

This means that employees no longer have to be physically present in an office or meeting room to conduct their daily tasks. Instead, they can now work from home, or wherever else suits them best. This also allows for greater flexibility when scheduling meetings and collaborating on projects.

Therefore, it’s important to find a collaboration tool that will help you manage your time effectively. Double booking, wrong meeting preferences, and missed deadlines are just some of the problems that can occur if you don’t use a reliable platform.

That’s where Microsoft Bookings and Calendly come into play. Both tools offer similar features, but each one excels in different areas.

In this detailed comparison article, we’ll take a look at these differences, as well as highlight the best & unique features of each, meeting scheduling tool.

Without any delay, let’s get started.

Microsoft Bookings VS Calendly: A Quick Side-by-Side Comparison!

Both cloud-based solutions provide users with access to many great features. However, there are certain key differences between the two. Let’s take a quick look at what makes both tools so special.


Microsoft Bookings


Offers four affordable pricing plans, starting at $9 per month. 

You need to buy a complete Office 365 subscription plan, which starts at 6$ per month.

User Interface

Very easy to navigate and offers a clean interface. It’s simple to create new events and even edit existing ones. 

The interface is quite cluttered and not user-friendly. You cannot easily add new appointments, change event details, or edit existing ones.


Offers a wide range of customization options. For example, you can custom emails, SMS notifications, and even set up reminders.

You only have access to basic customization options such as meeting scheduling, email templates, and calendar views.


Allows users to collaborate with others using Google Drive, Dropbox, OneDrive, and other cloud storage services.

Doesn’t support other cloud storage except for OneDrive.


Integrates with many popular apps like marketing, sales, payment processors, CRM, etc.

Microsoft Bookings supports integration with only Microsoft Apps.

Automatic Workflows

Supports Automatic Workflow, which allows you to automate certain processes within the app.

Does not support automatic workflow

Time Zone Detection


Not Available

Calendar Management 



Employee Scheduling



Group Scheduling


Not Available

Support Quality


Not So Good

Calendly VS Microsoft Bookings: Comprehensive Overview!

When comparing Calendly and Microsoft Bookings, both tools offer a wide range of functionality. Let’s take a look at a quick overview and key features of both booking apps.

What Is Calendly - A Quick Overview!

Calendly is a cloud-based calendar app that helps users plan events, such as meetings and conferences. It offers a simple interface that makes it easy to create new events, invite attendees, and set reminders.

It works across all devices, including smartphones, tablets, laptops, and desktops. The app also integrates seamlessly with other services like Google Calendar, Outlook, and iCloud.

With Calendly, you can easily share your event details with others, and even add notes to specific dates. You can also send invitations via email, SMS, or social media channels.

Furthermore, you can search your entire calendar by date, location, or keyword. If you’re looking for something specific, you can filter your results using filters like “Meeting”, “Conferences” or “Birthdays”.

Calendly is a complete solution for organizing your day-to-day activities from meeting scheduling to payment processing to project management.

Key Features Of Calendly

1. Automated Workflows

Time is everything, especially when it comes to running a successful business. That’s why Calendly automates many processes so that you can focus on what matters most.

With Calendly workflows, you can create responses for meetings automatically, assign tasks to team members, and more. Invitation and confirmations emails to improve attendance rates, and automatically update your calendar with responses.

Moreover, personalized responses via emails or SMS messages make sure that everyone receives the information they need. So, whether you want to schedule a conference call, or simply inform someone about a change in plans, Calendly has got you covered.

2. Real-time & Accurate Scheduling

Scheduling meetings are never fun, but it doesn’t have to be stressful either. With Calendly, you don’t have to worry about missing out on important appointments because of inaccurate schedules.

Your availability is always up-to-date, and you can send invites to multiple people at once. Plus, Invitees receive an automated confirmation message if they accept or decline your invitation.

Invitees can choose a suitable time slot based on their preferences, and you can even see who accepted or declined your request. This way, you know exactly how many people are attending your meeting, and you can adjust accordingly.

3. Full Control On Admin Management

You can manage every aspect of your company’s calendar. Whether you want to edit existing events, delete them, or create new ones, Calendly gives you full control over your data.

Plus, you can create groups of events, which allows you to organize your calendar into different categories. For example, you could create one group for sales calls, another for client visits, and still another for product launches.

You can invite members as admins or simple users, and you can even set permissions for each member. This means that only those users who need access will get it.

That’s not all! View and manage all users in one place, and keep track of all changes made to your calendar.

4. Compatible With Popular Calendars

Many companies use Google Calendar, Outlook, and other popular calendars. Now, you can sync your Calendly account with these services.

This means that you can view your events in real-time without having to log into any other service. Plus, you can import events or schedules from Google Calendar, Outlook, and others.

5. Wide Range Of Integrations

To help you run your business better, Calendly integrates with dozens of apps and services. The automation of any workflow is necessary for today’s businesses.

Calendly helps you automate your business by integrating with popular tools like Slack, Zapier, and more. You can also integrate with third-party systems such as Salesforce, HubSpot, and more.

Whether you want to integrate with marketing platforms, payment processors, analytics tools, CRM, or anything else, Calendly makes it easy.

Calendly Pros & Cons - Is It Legit Or Not?

Pros Of Calendly

  • Free trial for 14 days to test the app before purchasing. And, no credit card is required.

  • Customizable options for invitees as well as admins.

  • User-friendly interface.

  • Real-time scheduling with complete visibility.

  • Sync with various online calendars.

  • Send guests your Calendly link for quick registration.

  • Easy integration with popular apps and services.

  • Send automatic reminders, updates, and notifications.

  • Schedule your website without no coding needed.

Cons Of Calendly

  • Limited features in the free and basic versions.

  • You may need to understand a bit about customizing the workflows.

Pricing Overview Of Calendly - Is It Worth Your Money?

Definitely, yes! If you’re looking for an affordable yet powerful solution for managing your meetings, then Calendly is worth checking out.

It has tons of useful features, and its pricing plan is very reasonable. So, if you’re planning on using this tool for your business, we highly recommend it. Following are the 4 plans offered by Calendly.

  • Basic Plan (Free): Suitable to test Calendly, this plan includes some basic features.

  • Essentials Plan ($9/month/seat): This plan offers most of the features available in the Basic Plan plus additional ones at affordable prices. Moreover, it is a good choice for 2 calendar connections per person.

  • ProfessionalPlan ($12/month/seat): For medium-sized teams, this plan provides all the features of the Essentials Plan plus 6 calendar connections per person.

  • Teams Plan ($16/month/seat): Unlock unlimited advanced features including team management, recurring meetings, and much more. Plus you can try this plan for 15 days for free with no credit card.

  • Enterprise: If you have a large number of users, this plan will be perfect for you. With this plan, you get access to all the features of the Teams Plan along with unlimited seats. Contact their support team for details.

What Is Microsoft Bookings - A Quick Overview!

Cloud-based service that allows you to manage events, meetings, and bookings from one place. Microsoft Bookings is the services or scheduling tool used by many companies and small businesses.

With Microsoft Bookings, you can create, edit, and schedule any type of event, meeting, or booking. But the users of Microsoft 365 Business members can use this platform for free.

This cloud-based application is compatible with iOS and Android mobile devices, and web browsers.

From scheduling meetings with customers to creating events for employees, Microsoft Bookings helps you organize everything. You can also send invitations to attendees, set up reminders, and track attendance.

In addition, you can share your calendar with other people via email, text message, and social media.

Best Features Of Microsoft Bookings

1. Customizable Booking Pages

Giving a professional look to your events, meetings, and appointments is easy with Microsoft Bookings.

You can customize the pages of your events, meetings, or bookings. Moreover, your customers can choose the available options when they receive the invitation.

2. Calendar Integration

The integration of your calendars with Microsoft Bookings makes it easier for you to keep track of your events.

But, Microsoft Bookings works only with Outlook or Microsft calendars. Those who don’t use these two applications can not sync their Google, Apple, iCloud, Yahoo, and other calendars.

3. Invitations And Reminders

Inviting guests to your events, meetings or bookings is simple with Microsoft Bookings. You can easily add them as attendees, send them a reminder, and even change the time of the event.

Moreover, you can also set up automatic reminders so that you don’t forget about an important appointment.

4. Manage Teams Members Seamlessly

Many businesses need admin, viewer, organizer, and moderator roles. However, Microsoft Bookings got you covered

It lets you assign different roles to each user based on their permissions to your calendars. So, you can give admin rights to those who need them while keeping everyone else limited to viewing and organizing events.

5. Integrations

When it comes to integrating third-party apps with Microsoft Bookings, then you will be disappointed. It doesn’t work with most popular apps like Gmail, Slack, Trello, etc.

However, this scheduling tool works only with all Microsoft apps including Office 365, Skype for Business, OneDrive, etc. So, if you are using any of these products, then you can integrate them with Microsoft Bookings.

Pros & Cons Of Microsoft Bookings - Is It Legit Or Not?


  • A powerful yet affordable scheduling app, then Microsoft Bookings is perfect for MS 365 users.

  • Automated responses, reminders, and notifications make it easy for you to handle your events, meetings, bookings, and more.

  • The customization feature gives you full control over your events, meetings, etc.

  • Compatibility with multiple platforms (iOS, Android, web).

  • Assign roles to different users based on their permissions.


  • No support for non-MS365 accounts.

  • No third-party integrations, as it works only with Microsoft apps.

Pricing Overview Of Microsoft Bookings - Is It Worth Buying?

As Microsoft Booking is part of MS 365 business subscriptions, so you need to purchase an Office 365 business subscription in order to get access to this service.

If you want to try out Microsoft Bookings without purchasing anything, then you can sign up for its free trial version of Office 365. The starting paid plan is $6 per month for 1 user.

But, you need to provide your credit card details during registration. After which, you will have 30 days to cancel your subscription, if you don’t find it useful.

Conclusion - Final Thoughts!

As you can see, both tools offer similar functionality, however, Microsoft Bookings has more limitations compared to Calendly.

If you’re looking for a powerful yet flexible tool to manage your business’ schedules, then Calendly should definitely be your first choice.

It’s free, easy to use, and packed full of useful features.

On the other hand, if you are a small business owner who wants a solution that is cost-effective and easy to implement, then Microsoft Bookings might be a better option for you. And If you are a user of an MS Office 365 business subscription, then you will get it free.

Calendly offers more integrations, advanced customization options, and automatic workflows. But if you can rely only on MS products or Apps, then Microsoft Bookings may be a better fit for you.

We hope this detailed comparison helped you decide between the two tools. So, make a wise decision by choosing one of them according to your needs.

President at Hoopis Group | Website | + posts

Peter Hoopis is CEO of Hoopis Group and author of the new book E-Cruiting, which leverages his almost three decades of experience in recruiting Financial Services Professionals. Peter specializes in mentoring, training, and developing Financial Services managers and making them better recruiters and helping them grow their firms. In his spare time, he enjoys camping with his children and driving his race car; he is a purple belt in Brazilian Jiu-Jitsu. He lives in Chicago with his wife Melissa and four children.