Microsoft Bookings Vs Calendly: 2023 Comparison

Microsoft Bookings Vs Calendly

If you’re looking for a way to make scheduling appointments and meetings easier, two popular solutions are Microsoft Bookings and Calendly, but what’s the difference? To make your decision easier, we wrote this comparison of Microsoft Bookings vs Calendly.

We’ve broken down our review into an overview of each product with pros and cons, followed by comparisons of the booking plugins in four main categories: features, ease of use, customer service, and pricing. 

By the time you finish reading, you should have a much better idea of whether Calendly or MS Bookings is best for your personal and professional needs and goals.

Microsoft Bookings and Calendly: What Are They For?

Trying to decide between MS Bookings vs Calendly can be hard because they are very similar tools. Both can be used to effectively book appointments for meetings, interviews, calls, and other one-on-one or group activities.

In a broad sense, these apps are meant to save you time, eliminate the need to email back and forth to schedule appointments, and improve the quality of your customer service. Calendly and Microsoft Bookings can both be customized to suit different types of businesses.

Microsoft Bookings Vs Calendly: Overview

Overview of Microsoft Bookings

calendly vs microsoft bookings

Microsoft Bookings is a Microsoft Calendly alternative that you can purchase as part of Microsoft 365, which is the company’s suite of other business tools. So, if you already use MS 365, Bookings is already included for you to access at no additional cost.

Pros of MS Bookings

  • Works well for people who use other Microsoft 365 software
  • Can add employees who don’t have a 365 account
  • Step-by-step implementation guides available

Cons of MS Bookings

  • Can only be purchased as part of Microsoft 365
  • Limited customizability and features
  • Learning curve to get the hang of using

Overview of Calendly

microsoft calendly alternative

Calendly is a popular appointment booking application that has been around since 2013. Once you sign up for the software and sync it with your calendar, you can share a unique link or embed Calendly on your website to allow customers, clients, or team members to grab an open time on your calendar.

Pros of Calendly

  • Very easy to use
  • Basic version is 100% free
  • Highly customizable
  • Lots of integration with different apps and calendars
  • Easy and intuitive to use

Cons of Calendly

  • Free version has limited features
  • Interface can feel overly basic
  • Can be unclear how many people confirm attendance to appointments

Features and integrations

Microsoft Bookings features and integrations

Microsoft Bookings provides all the basic features you need to schedule and manage appointments. It integrates seamlessly with your Outlook calendar and all of Microsoft’s other business tools. MS Bookings does not sync with other tools and platforms outside the Microsoft ecosystem. Bookings does not allow you to accept online payments, either.

Calendly features and integrations

Like MS Bookings, Calendly has all the basic features required to schedule meetings and appointments, including the ability to accept individual and group bookings. You can sync Calendly with Google Calendar or your Outlook calendar. 

Calendly also has many other integrations with popular business tools, including HubSpot, Mailchimp, Zapier, and more. Additionally, you can accept online payments via Calendly through PayPal and Stripe integrations.

Calendly vs Microsoft Bookings winner in features and integrations: Calendly

Calendly wins against Bookings in the features and integrations category because it has many more than the Microsoft scheduler software. 

Both tools can work fine for scheduling simple meetings, but if you want a scheduling app that’s much more flexible and robust in terms of features and integrations that help you do business, Calendly is the clear winner.

Ease of use

Microsoft Bookings ease of use

Many people who have used Microsoft Bookings note that there can be a fairly moderate learning curve to get accustomed to the tool. Although there are many online resources to help you learn how to implement Bookings, it doesn’t have a very intuitive interface or design.

Calendly ease of use

Calendly is incredibly easy and intuitive to use, and most people are able to get the hang of its basic functionality very quickly. Since Calendly integrates with so many different work platforms, it’s very easy to implement into your existing workflows.

Calendly vs Microsoft Bookings winner in ease of use: Calendly

Calendly wins again in the ease-of-use category because it’s so simple and fast to get started with the booking plugin, not to mention it’s super easy for your customers or clients to use, as well.

Customer service

Microsoft Bookings customer service

Microsoft Bookings has lots of different customer service options available, including online and phone support. There is also an extensive online knowledge database and video tutorials that you can access for self guidance.

Calendly customer service

Calendly’s customer service is available to contact online. The company’s site also has online resources and a help center that you can browse to learn how to use Calendly.

Calendly vs Microsoft Bookings winner in customer service: MS Bookings

Microsoft Bookings beats Calendly in the customer service category because Microsoft offers phone support and Calendly doesn’t.


Microsoft Bookings pricing

Microsoft Bookings is included with any subscription to Microsoft 365. Subscriptions start at $6.00/user per month for a Business Basic plan. There is also a one-month free trial of MS Bookings available.

Calendly pricing

calendly pricing comparision

The Basic version of Calendly is totally free, and paid plans start at $8.00/user per month for the Essentials package.

Calendly vs Microsoft Bookings winner in pricing: tie

There is no clear winner in the battle between Microsoft Bookings vs Calendly in terms of pricing structure, so we are declaring this category a tie!

Since Bookings is included as part of 365, you’re getting access to a whole bunch of different tools for the same price. Calendly has a free version, but it’s only the scheduling software. 

The better pricing structure for you really depends on your personal needs and what you want to get out of your subscription to either product.

Microsoft Bookings and Calendly: Which One Should You Choose?

When should I choose Microsoft Bookings?

Microsoft Bookings works best when you already use Microsoft 365 for other business purposes and you want a piece of scheduling software that integrates with your Outlook calendar and works within the Microsoft ecosystem of tools and platforms.

MS Bookings is not really suited to service-based businesses, since it doesn’t let you accept online payments and it is not intuitive to use for customers. The platform is mainly geared towards small businesses and scheduling internal team meetings or meetings with clients.

When should I choose Calendly?

Calendly is suited to a much broader category of business types, including service providers, freelancers, consultants, and others. Because of the option to accept payments at the time of booking, it’s definitely a better choice than MS Bookings for service-based businesses.

All the different integrations and features of Calendly also make it a good choice for sales and marketing professionals who use platforms like HubSpot and Mailchimp to make sales and track customer activities.


Calendly and Microsoft Bookings are two solid options you have when it comes to appointment scheduling plugins. 

Based on our review and comparison of both products, we think that Calendly has a broader range of use cases than Bookings, but Bookings can definitely work for many people with more basic needs.

If your website is built with WordPress there’s an even better solution to manage appointments. WEBBA Booking is an easy-to-use plugin that’s equipped with all the necessary features to allow appointment booking from your website. It’s easily scalable by, for example, offering an online payment option or Google Calendar integration. You can try the free version or unlock premium features right away.

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