Calendly vs. MS Bookings: A 2026 Comparison of Popular Scheduling Apps

Any business operating in today’s world needs a scheduling tool.

Automated scheduling improves your productivity and time management and gives customers a better experience when dealing with your business.  

Like any industry, though, there are a bunch to choose from. Today, we’ll zoom in on two popular options: Calendly and Microsoft (MS) Bookings. 

Whether you're a professional looking for a no-frills scheduling app or a business needing a robust booking system, we’ll walk through everything you need to know to pick the best solution for your team.

Calendly is a user-centric scheduling tool that makes booking super easy. Its user-friendly interface and various advanced features have made it a top choice for professionals and businesses. 

Calendly's not-so-secret recipe is its personalized booking link. Users can share it with invitees, who can view availability and select a time slot that works for them. The seamless integration with popular calendars, including Office 365, Outlook, and Google Calendar doesn’t hurt either, ensuring your booking link is always up-to-date.

Calendly key features include:

• Easy link sharing: Effortlessly share your booking link.
• Google Calendar, Outlook, and Office 365 integration: Keep your schedule in sync.
• User-focused interface: Straightforward, intuitive design.
• Diverse meeting types: Customization options for various agendas.

Goh X., a small business manager, explains the pros and cons of using Calendly:

Calendly customer ratings

MS Bookings delivers functions well beyond scheduling. MS Bookings offers a seamless experience for those using the suite—integrated into every part of the Microsoft ecosystem. 

Bookings is your all-in-one scheduling solution, letting you create events, set reminders, and invite attendees, all within the familiar Microsoft environment. Advanced integration with other Microsoft tools, such as MSTeams, brings your scheduling to the next level.

MS Bookings key features include:

• Comprehensive integrations: Deeply connect with other Microsoft tools.
• Advanced scheduling: Automate appointment confirmations, reminders, rescheduling, and cancellations.
• Staff management: Efficiently manage team schedules.

Rosie H., CEO of a marketing and advertising company, delves into the benefits and drawbacks of Microsoft’s scheduling solution: 

MS Bookings customer ratings

Who is Calendly for?

If you’re looking for a scheduling app that’s user-friendly and versatile, and integrates with many different tools, Calendly will be your best bet. 

Calendly’s advanced features and flexibility will let you smoothly manage different kinds of meetings, regardless of your business type. Additionally, its ability to sync with over 150 diverse tools lets Calendly plug into your existing workflow easily.

Who is MS Bookings for? 

If you faithfully use apps in the Microsoft ecosystem, MS Bookings might be the tool for you. It’s a scheduling solution that’ll streamline your booking process and intuitively connect with other Microsoft tools.

As it’s included in a Microsoft 365 Business subscription (not available to those on individual plans) along with apps like Word, Excel, and Outlook, Bookings will also be a good choice for individuals and businesses looking for solutions outside of only scheduling.

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Calendly

Calendly offers a user-friendly experience. Potential clients just click on the appointment link, select the desired meeting/event type and time, and provide their contact details. Once they’ve booked a slot, they’ll get a confirmation email. 

Calendly can support communication with any number of invitees (and different time zones) and gives the option for individual or group bookings. Its mobile functionality also guarantees compatibility across devices. 

Microsoft Bookings

Designed for Microsoft 365 users, Bookings provides a simple scheduling process. Invitees can choose from available time slots and book appointments with precision and confidence. Multiple staff members can use this system, while clients and colleagues can access other team members’ schedules. 

Compared to Calendly, MS Bookings will likely be a bit more complicated and time-consuming to set up, but the platform still offers an intuitive design and handy booking options. However, you might find that MS Bookings has fewer integrations compared to Calendly, which can be a pain for some users.

The two online schedulers share a few features typically found in the top scheduling apps, including: 

• Customizable booking pages
• Automatic notifications, including email confirmations and SMS and email reminders
• One-on-one and group scheduling
• Virtual and in-person meetings
• Buffer times between meetings
• Multiple appointment types and lengths
• Add a minimum notice period for scheduling with you
• Configurable booking form
• Time zone detection
• Automatic calendar invites

Calendly’s unique features

Calendly offers quite a few features that MS Bookings lacks, including: 

• Round-robin scheduling
• Meeting polls so that participants can vote on the best time to meet
• Activity dashboard with meeting analytics
• Routing logic via booking forms
• iOS and Android apps (MS Bookings discontinued their mobile apps in 2023)
• More personalized branding and customization, including removing Calendly's logo and watermark
  
• Lead routing with CRM account lookup
• Payment processing (Stripe and PayPal)

Calendly limitations

As it’s a standalone app, you only get access to a booking tool when you opt for Calendly. If you’re looking for a package deal with other apps, MS Bookings comes as part of a more extensive suite of Microsoft tools, so if you work within the Microsoft sphere, MS Bookings is the better choice.

MS Bookings’ unique features

MS Bookings is a simple scheduling tool that shines because it's part of the broader suite of Microsoft apps. However, when it comes to scheduling features alone, it doesn't bring anything to the table that Calendly doesn't already offer.

MS Bookings limitations

Aside from the somewhat limited scheduling features, MS Bookings’ main drawback lies in its inability to connect with apps outside the Microsoft suite. This can make it an inconvenient tool to work with if you aren’t an avid Microsoft user. 

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A closer look at Calendly’s integrations

In the battle of integrations, Calendly comes out on top with over 150 tools in its scheduling arsenal, while Bookings only integrates with apps within the Microsoft suite.

Here are a few of Calendly’s standout integrations:

• Calendars: Google, Outlook, and Exchange

• Video conferencing: Zoom, Google Meet, Microsoft Teams, Webex, GoTo Meeting, and Join.Me

• Online payments: Stripe, PayPal, and Stax Payments

• CRMS: Salesforce, HubSpot, ActiveCampaign, Gong, Zoho, Close, and Postal

• Other: Slack, Mailchimp, Zapier, Google Analytics, Gmail, WordPress, Squarespace, Notion, and Typeform

A closer look at MS Bookings’ integrations

MS Bookings’ only native integrations are the apps available in Microsoft 365, including:

• Microsoft Word, Excel, PowerPoint, and OneNote
• Outlook Mail
• OneDrive
• Microsoft Teams
• SharePoint
• Microsoft 365 Copilot 

Although Calendly also integrates with a few of those apps, Bookings offers a deeper sync with the tools.

For example, while Calendly integrates with Microsoft Teams, the capabilities are limited to automatically generating unique Teams video conference links, while MS Booking has a more nuanced integration. You can add MS Bookings directly to MS Teams, allowing you to book and edit meetings without leaving the conferencing app. 

Calendly’s pricing and plans

Calendly’s plans (billed annually) include:

• Free plan with basic scheduling features and one calendar connection
• Standard plan ($10/month/user) for smaller teams and individuals, offering multiple calendar connections and various meeting types
• Teams plan ($16/month/user) for larger teams, with admin tools and round-robin meetings
• Enterprise plan (starting at $15,000/year) created for teams of 30 or more, providing advanced security, control, and support

Calendly offers a 14-day free trial of its Teams plan.

Microsoft Booking’s pricing and plans

Unlike Calendly, MS Bookings isn’t a standalone tool—it’s only one of many apps included in a Microsoft 365 subscription. Therefore, choosing between the following plans won’t be based on the scheduling features you’re looking for, but rather on the Microsoft capabilities at your disposal.

The plans (billed annually) include:

• Business Basic ($6/user/month) with access to Word, Excel, PowerPoint, and Outlook web and mobile apps, a custom business email, and four secure cloud services 
• Business Standard ($12.50/month/user) with desktop versions of Word, Excel, PowerPoint, and Outlook, webinars, and video editing tools
• Business Premium ($22/month/user) with everything featured in the other tiers, plus advanced cyber threat protection and identity management

Although Microsoft doesn’t offer a free plan, you can opt for a one-month trial of the plan of your choosing.

Need more perspective on both scheduling tools? It’s time to turn to real-life users who can offer deeper insights into the pros and cons of Calendly and Microsoft Bookings.

Customer feedback on Calendly

Erin S summarizes her thoughts about the popular scheduling app: 

What do you like best about Calendly?

No more back and forth with customers. It always felt like I was berating them just to get the meeting set up. Now I can focus on the agenda and what is important content for that meeting!

What do you dislike about Calendly?

There are not many downsides. I don't like that I get 2 emails in reply to new appts getting set. Clogs my inbox. Also, I would like for the name and emails to be visible in the invite when I have multiple spots available in a session.

Mwendwa N., a senior marketing analyst, expands on their experience using Calendly:

With Calendly's group scheduling feature, several users can reserve timeslots at once. By setting buffer times between meetings, users of the platform can allocate time for preparation or breaks. Calendly makes it simple for participants to reschedule meetings, preserving flexibility for all involved.

What do you dislike about Calendly?

More comprehensive analysis of scheduling patterns and participant behaviour would be helpful. Only the premium plans offer more sophisticated branding and customization options.

Customer feedback on MS Bookings

Lindsey J., a ranger trainee, explains what she likes and dislikes about the booking tool:

What do you like best about Microsoft Bookings?

I love that Microsoft Bookings makes it easy for me to set up interviews, appointments, and meetings with minimal effort on my part. I like that bookings show up directly in my calendar after they’re created.

What do you dislike about Microsoft Bookings?

The one thing I dislike about Bookings is the fact that you can't set multiple weeks at a time. For example, my availability changes every week. I don't always work the same days or times. When I set up a booking option for an interview with me, I need to create an option for each week which can occasionally be confusing for my interviewees when they attempt to book with me.

Elisha S., an operations manager, shares why her team switched from Calendly to MS Bookings:

What do you like best about Microsoft Bookings?

I love how easy it was to setup! It is one of the main reasons we switched over to Microsoft! Bookings allowed us to maximize our license and move to Microsoft from Calendly.

What do you dislike about Microsoft Bookings?

It would be nice to receive a notification when someone cancels a meeting, or be notified in the calendar when they cancel. Right now the only way we are aware of for clients to cancel a meeting is to go into the invite and cancel on the web page.

👉 Calendly is the go-to solution for professionals and businesses seeking a UX-enhanced, dedicated scheduling tool. Its advanced features, user-friendly interface, and flexibility in handling various meeting types make it a great choice. It’ll also be a better option if you use tools that aren’t part of the Microsoft suite, as Calendly offers integrations with over 150 different apps. 

👉 MS Bookings instead offers a broader set of functions within the Microsoft ecosystem. It's perfect for individuals and businesses deeply rooted in the Microsoft universe. It’s a feasible option with seamless MS integration and comprehensive scheduling capabilities. If you’re already paying for a Microsoft 365 subscription, give MS Bookings a shot to see if it fits your business well.

Ultimately, your choice between Calendly and Microsoft Bookings should align with your unique scheduling requirements. Whether you prefer the simplicity of Calendly or the comprehensive MS integration of Bookings, your schedules will become easier to create, edit, and manage. Both tools aim to simplify scheduling, freeing up your time to make the most of other business needs.

If neither Calendly nor Microsoft Bookings quite fits your scheduling needs, YouCanBookMe (YCBM) provides a more flexible middle ground. It’s built for individuals and teams who want greater control over customization and booking workflows without being tied to a single software ecosystem.

What makes YouCanBookMe superior?

Where Calendly focuses on speed and simplicity, and Microsoft Bookings prioritizes deep Microsoft 365 integration, YouCanBookMe is built for small businesses and professionals who care about first impressions and flexibility just as much as efficiency. Here are the key features that put YouCanBookMe above other scheduling tools on the market: 

• Deeper control over how bookings work: YouCanBookMe gives you fine-grained control over availability, meeting types, durations, buffers, and booking limits.
• Fully customizable, branded booking pages: Booking pages can be customized with your logo, colors, images, and messaging, creating a more professional first impression. You can also password-protect pages, enable request-only bookings, and control how availability is displayed—features that go beyond basic scheduling links.

• Automated notifications and no-show reduction: Confirmation emails, reminders, follow-ups, and SMS notifications can be tailored to different booking scenarios. These workflows help reduce no-shows and cut down on administrative work as booking volume increases.
• Advanced scheduling features for teams: YouCanBookMe supports advanced scheduling options such as round-robin scheduling and meeting polls. These features make it easier to distribute meetings fairly across teams or coordinate group availability.
• Payments, integrations, and global support: YouCanBookMe supports payments at booking via Stripe, including Apple Pay and Google Pay, and integrates with popular calendars, video tools, and thousands of apps via Zapier. With support for 40+ languages and automatic time-zone handling, it’s well suited to international teams.

"YouCanBookMe is an amazing tool for businesses, every type of business... From somebody that's a freelancer, because I know you have this amazing integration where you can actually take payments, up to really large businesses where they need more value and more flexibility and more in-depth features or integrations."
– Georgie Ionescu, Passion.io

Elevate your booking process

YouCanBookMe's superiority is not a singular trait but a triad of features that redefine the scheduling landscape. From its powerful notifications workflow to personalized availability views and unique booking controls, YCBM offers an unmatched scheduling experience.

Elevate your booking process, try YouCanBookMe today, and embrace the difference in scheduling efficiency.

FAQ about Calendly vs. MS Bookings

Which is better: Calendly or MS Bookings?

Your choice will hinge on your current toolset and the specific scheduling features you require. If you’re looking for a versatile and flexible booking app that’ll easily fit into many different workflows, Calendly will be your best bet. Its advanced features and integrations with over 150 tools make it a standout choice. In contrast, if you’re looking for a scheduling solution that deeply syncs with apps in the Microsoft ecosystem, MS Bookings might suit you better. Bundled with a Microsoft 365 subscription, it offers convenient access to other MS suite tools alongside its booking functionality.

What is the main difference between Calendly and MS Bookings?

The main difference between Calendly and MS Bookings lies in the apps each scheduling tool integrates with. While MS Bookings deeply syncs with tools within the Microsoft suite, it doesn’t provide integrations beyond that. Calendly, on the other hand, allows you to integrate over 150 different tools with its booking app. Additionally, while Calendly is a standalone scheduling solution, MS Bookings is part of a myriad of tools included in a Microsoft 365 subscription.

Which scheduling tool is more affordable: Calendly or MS Bookings?

If you’re looking for a free scheduling solution, Calendly is the way to go, as it provides a free plan, which MS Bookings lacks. However, for paid plans, MS Bookings offers greater affordability, granting access to the scheduling tool and other Microsoft apps (such as Word, Excel, PowerPoint, and Outlook) for just $6/user/month when paid annually. In contrast, Calendly’s most affordable paid plan comes in at $10/user/month when paid annually, but keep in mind it doesn’t offer access to all features.

Is there an alternative to Calendly and MS Bookings?

Yes. If neither Calendly nor Microsoft Bookings quite fits your scheduling needs, YouCanBookMe is a flexible alternative worth considering. It’s designed for individuals and teams who want more control over how bookings work.

YouCanBookMe provides deeper customization than both tools, including fully branded booking pages, advanced availability rules, request-only bookings, and customizable notifications to help reduce no-shows. It also supports advanced scheduling features such as round-robin scheduling and meeting polls, making it well suited for teams and more complex scheduling scenarios.

Unlike Microsoft Bookings, YCBM integrates widely outside one ecosystem, connecting with Google Calendar, Outlook, Zoom, Google Meet, Microsoft Teams, Stripe, and thousands of other tools via Zapier. It also supports payments at booking, multiple languages, and automatic time-zone handling, making it a practical option for growing or international businesses.

YouCanBookMe offers a generous free plan and a 14-day free trial on paid plans.