Microsoft Bookings vs Calendly: Which One Should I Choose?

Microsoft Bookings has seamless integration with Microsoft 365 Copilot

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microsoft bookings vs calendly comparison

Microsoft Bookings and Calendly are two popular scheduling tools designed to simplify appointment bookings. However, they cater to different audiences and integrate with different ecosystems. Here’s a comparison to help you choose the best option for your needs.

Microsoft Bookings vs Calendly

1. Overview

Microsoft Bookings is a dedicated scheduling tool for business users with a Microsoft 365 Copilot license. You can’t get it unless you have a working account. In contrast, Calendly is dedicated to individuals, freelancers, and small organizations. However, you can integrate it with Microsoft Teams, so you shouldn’t dismiss it for any kind of business.

FeatureMicrosoft BookingsCalendly
Best ForBusinesses using Microsoft 365Individuals, freelancers, teams
PricingIncluded with Microsoft 365 Business & Enterprise plansFree & paid plans (starting at $10/month)
Ease of useRequires Microsoft 365 setupVery intuitive & standalone
IntegrationMicrosoft 365, Outlook, Teams, SharePointGoogle Calendar, Teams, Outlook, Zoom, Slack, CRM tools

Considering that Microsoft Bookings has seamless integration of all the office apps, if your business is using the Redmond giant’s platform, you know what the right choice is. For small organizations or small teams, however, Calendly offers a modern and simple interface that offers everything you need. Plus, Calendly has a free version as well.

2. Features Comparison

FeatureMicrosoft BookingsCalendly
Calendar SyncSyncs with Outlook & Microsoft 365 calendarsSyncs with Google, Outlook, iCloud, Office 365
CustomizationCustom booking pages, branding optionsFully customizable booking links, workflows
Automated RemindersEmail & SMS reminders (via Outlook)Email, SMS (on premium plans), workflows
Meeting TypesOne-on-one, group bookings, staff schedulingOne-on-one, round-robin, group events
Payment IntegrationMicrosoft Pay (limited)PayPal, Stripe (on paid plans)
Embedding & SharingEmbed in Microsoft apps, public booking linkEmbed in websites, social media, public link
Mobile AppYes (iOS & Android)Yes (iOS & Android)

Microsoft has invested a lot in Bookings lately, introducing real-time Queue Experience for appointment management, and last year, the app was completely revamped. Calendly is not bad either, being constantly updated, and offering website and social media embedding for private or business purposes.

3. Key differences

✅ Choose Microsoft Bookings if:

  • You are already using Microsoft 365 for business.
  • You need tight integration with Teams, Outlook, and SharePoint.
  • Your business requires multi-staff scheduling with different services.
  • You prefer a more structured, business-oriented tool.

✅ Choose Calendly if:

  • You want a standalone and user-friendly scheduling tool.
  • You need better payment options like Stripe & PayPal.
  • You want advanced integrations with CRM, Slack, Zoom, and more.
  • You prefer affordable pricing for individuals and small teams.

4. Pricing comparison

PlanMicrosoft BookingsCalendly
FreeNo (only with Microsoft 365)Yes (basic features)
Basic/PremiumIncluded in Microsoft 365 Business plans ($6.99–$22/month)$10–$16/month per user
EnterpriseIncluded in Enterprise plansCustom pricing

Which one should I use, Microsoft Bookings or Calendly?

As we’ve mentioned above in this guide, Microsoft Bookings should be the clear choice if your business has a Microsoft 365 Copilot license. If you’re a freelancer or a small business manager, Calendly might get all you need for less money and more flexibility.

But these two are obviously not the only apps to consider. If you need more ideas, check our list of the best calendars for Windows. You might also be interested in our list of the best online scheduling tools.

Let us know in the comments below what app you’re using and why.

More about the topics: productivity software, task scheduler

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