Calendly vs. Microsoft Bookings: Which one should you use?

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Calendly vs. Microsoft Bookings: Uncover which scheduling software is right for you with our detailed comparison.

Free - $20/mo (per seat)
$6/mo - $22/user/mo
Best For:
Everyone from small businesses to Fortune 100 companies looking for a tool to make scheduling (and remembering) meetings easier.
Best For:
Small and enterprise businesses
Free - $20/mo (per seat)
Best For:
Everyone from small businesses to Fortune 100 companies looking for a tool to make scheduling (and remembering) meetings easier.
$6/mo - $22/user/mo
Best For:
Small and enterprise businesses

In the bustling world of digital scheduling, two platforms stand out – Calendly and Microsoft Bookings.

Each offers a unique spin on scheduling appointments, meetings, and events, but which one is right for you? 

Are you wondering about the differences between these platforms? Look no further, as our in-depth Calendly vs. Microsoft Bookings comparison will provide the answer you seek.

Calendly vs. Microsoft Bookings at a Glance

CriteriaCalendlyMicrosoft BookingsWinner
SMB Guide’s Rating9/107/10Calendly
Appointment Workflow AutomationTie
Customization OptionsTie
Calendar Management FeaturesSync with Google, iCloud, Outlook, and Exchange calendarsLimited optionsCalendly
Automated Reminders and NotificationsTie
Client Management & CommunicationMicrosoft Bookings
UX and UIHigh user-friendlinessHigh user-friendlinessTie
Integrations & API Capabilities100+ integrationsMicrosoft productsCalendly
Supported PlatformsWeb-based, iOS and Android mobile appsWeb-based, iOS and Android mobile appsTie
Customer SupportLive chat, automated chat box, email support ticketsLive chat, email, help center, phoneMicrosoft Bookings
PricingFree – $20/mo (per seat)$6/mo – $22/user/moCalendly
ScalabilityHighly scalableHighly scalableTie

Calendly: Key Features, Pros, Cons, & Pricing

calendly homepage

Calendly is a popular appointment scheduling software known for its vast array of features designed to streamline the scheduling process.

It integrates with multiple calendar applications to allow for seamless synchronization of schedules and appointments across platforms.

It also offers website embedding capabilities so clients can conveniently book appointments directly from a business’s website.

Pros & Cons


Free forever plan

iOS & Android apps

100+ integrations

Easy to build workflows


Too many features

Expensive for larger teams


Calendly offers four plans – one of which is the Free Forever plan. Paid plans start at $12/user/month or $10/user/month with annual billing.

If you require more than 30 users, you must invest in the Enterprise plan, which involves a custom price quote.

  • Free: Unlimited meetings with one event type and one calendar.
  • Standard: Adds group and collective event types, multiple calendars, reminders, reconfirmation requests, and additional workflows. You also get more integrations and live chat support.
  • Teams: Adds Salesforce CRM integrations, round-robin events, lead routing, and event templates.
  • Enterprise: Adds single sign-on, compliance features, domain claiming, additional Salesforce lead routing features, and prioritized customer support.

Microsoft Bookings: Key Features, Pros, Cons, & Pricing

microsoft bookings homepage

Microsoft Bookings is a versatile appointment scheduling software known for simplifying the process of managing and scheduling appointments.

One of the key features is the web-based booking calendar, which allows people to view, modify, and reschedule appointments easily.

It integrates with Outlook to optimize staff calendars and provide customers with the flexibility to book a time that suits them.

Pros & Cons


Easy to use

iOS & Android apps

Notifications and reminders

Customer-facing booking page


No free version

Lack of group scheduling features


Microsoft offers a few plans to choose from:

  • Microsoft 365 Business Basic: $6/month/user with annual billing and automatic renewal. It includes web and mobile versions of Word, Excel, Powerpoint, and Outlook; chat, call, and meet up to 300 attendees, 1 TB of cloud storage for each user, business-class email, manage customer appointments, 24/7 phone and web support, and standard security.
  • Microsoft 365 Business Standard: $12.50/month/user with annual billing and automatic renewal. It includes everything in Basic plus, desktop versions of the apps, webinar hosting, attendee registration, and reporting tools, tools to create personalized documents and layouts
  • Microsoft 365 Business Premium: $22/month/user with annual billing and automatic renewal. It includes everything in Business Standard, plus: advanced security, access and data control, and cyber threat protection.
Microsoft Bookings

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Appointment Workflow Automation

Both platforms make it super easy to get set up and accept appointments in no time. You’ll spend time setting up services/meeting types, available working hours, etc.

However, once the initial setup is complete, both platforms have client-facing online booking pages that make it easy for clients to schedule or modify appointments on their own.

✅ Winner: Tie

Customization Options

Customization options are limited on the free Calendly plan, but on the paid plans, you can add multiple types of appointments to the mix.

You can also customize the URL of your scheduling page and individual URLs for different event types.

calendly branding options

With the Standard plan and higher, you can add your branding and remove Calendly’s.

If you’re on the free plan, you’re stuck with Calendly branding, but you can still add your company logo for some branding.

With Microsoft Bookings, you can change the colors of the booking site, add your logo, etc., to ensure your booking page matches the look and feel of your company website.

You can choose a physical location or set online meetings with Microsoft Teams. Both tools allow you to add buffers between meetings so you have downtime.

✅ Winner: Tie

Calendar Management Features

Calendly integrates with Google, Outlook, iCloud, and Exchange, so you can prevent double-booking.

Using the free plan, you can sync appointments to one calendar, but the paid plans increase that to 6.

calendly calendar management

Microsoft Bookings, on the other hand, only integrates with Microsoft Outlook. Because of this, Calendly wins here.

✅ Winner: Calendly

Automated Reminders and Notifications

Both tools make it possible to send reminders via email or SMS. Calendly requires a paid plan to add SMS reminders and notifications.

It’s included on all the Microsoft Bookings plans, but it’s a tie simply because there is no free Microsoft Bookings option.

✅ Winner: Tie

Client Management and Communication

Calendly does not store meeting information of any kind of a client database.

If you need that functionality, you must use Microsoft Bookings or another scheduling software with similar features.

✅ Winner: Microsoft Bookings

User Experience and User Interface

Both tools offer an easy-to-use interface that makes for an excellent user experience.

You do not have to have any level of expertise or technology knowledge to put either of these tools to work for you.

✅ Winner: Tie

Integrations & API Capabilities

With Calendly, you get over 100 integrations with third-party applications, including project management, applicant tracking systems, and marketing automation tools.

calendly integrations

With Microsoft Bookings, there are only integrations with other Microsoft products.

That’s fine if you work solely within the Microsoft ecosystem, but if you have outside tools, Calendly is more practical.

✅ Winner: Calendly

Supported Platforms

Both platforms are primarily web-based, so you can access them from any device that has an internet connection.

Both tools also offer mobile apps for Android and iOS.

✅ Winner: Tie

Customer Support

When it comes to support, your options are limited on the Calendly free plan. You need a paid plan to get access to live chat.

Ultimately, Microsoft Bookings offers additional support options – beyond live chat, email, knowledgebase, and help center.

They also offer phone support, which is why they win over Calendly.

✅ Winner: Microsoft Bookings


Both platforms charge by the month, per user on the account. Calendly wins overall, because it offers a free forever plan, and even the most expensive plan option is still cheaper than Microsoft Bookings.

Plus, with Calendly, you can pay by the month, and with Microsoft Bookings, you must pay annually.

✅ Winner: Calendly


Both tools will grow with your business needs. You can have up to 30 users before you have to upgrade to Calendly’s enterprise plan with custom pricing.

✅ Winner: Tie

Standout Features of Calendly

Calendly provides options for meeting polls to add an extra layer of interactivity and flexibility to the scheduling process.

Standout Features of Microsoft Bookings

There aren’t really any standout features I could find in Microsoft Bookings that I didn’t see in all the major competitors, too.

If I had to pick one, it would be the next-level data security in the top-tier plan.

Calendly vs. Microsoft Bookings: SMB Guide’s Verdict

While both platforms work well to schedule virtual meetings, Calendly wins overall because it’s more affordable and easier to use.

It has a wider array of integrations and customization options.

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Lucinda has spent the last 15 years working from home as a freelance writer and WordPress designer, and throughout her career, she has worked directly with several digital marketing agencies with clients in the SaaS space, ranging from e-commerce platforms to procurement software.