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Scheduling & Booking

Calendly vs Microsoft Bookings

Which scheduling & booking tool is right for you? Compare features, pricing, and user reviews to make the best choice.

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Calendly

4.72,000 reviews

Individuals and teams that need fast, self-serve scheduling for sales calls, recruiting interviews, customer success check-ins, and paid appointments—especially organizations standardizing scheduling across multiple reps.

Starting at $10/user/month
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Microsoft Bookings

4.31,800 reviews

Microsoft 365-centric small and mid-sized businesses and internal teams that want simple, reliable appointment scheduling tied directly to Outlook/Exchange calendars (e.g., professional services, IT/helpdesk, HR, education, healthcare admin, and customer-facing appointment teams).

Starting at ~$6/user/month (via Microsoft 365 Business Basic)

Side-by-Side Comparison

FeatureCalendlyMicrosoft Bookings
Pricing$10/user/month~$6/user/month (via Microsoft 365 Business Basic)
G2 Rating4.7 (2,000 reviews)4.3 (1,800 reviews)
Capterra Rating4.74.0
Best ForIndividuals and teams that need fast, self-serve scheduling for sales calls, recruiting interviews, customer success check-ins, and paid appointments—especially organizations standardizing scheduling across multiple reps.Microsoft 365-centric small and mid-sized businesses and internal teams that want simple, reliable appointment scheduling tied directly to Outlook/Exchange calendars (e.g., professional services, IT/helpdesk, HR, education, healthcare admin, and customer-facing appointment teams).

Pros & Cons

Calendly

Pros

  • + Very easy for invitees to book without back-and-forth emails
  • + Reliable calendar sync and conflict prevention across major calendar providers
  • + Strong team scheduling options (round-robin/collective) for revenue and support teams
  • + Large integration ecosystem and automation options for common workflows

Cons

  • Some advanced features (routing, deeper automations, admin controls) require higher-tier plans
  • Customization/branding and complex availability rules can be limited compared with some enterprise-focused schedulers
  • Costs can add up for larger teams when multiple users need paid features

Microsoft Bookings

Pros

  • + Included with many Microsoft 365 business plans, reducing incremental software cost
  • + Tight Outlook/Exchange integration helps prevent double-booking and keeps calendars in sync
  • + Easy to deploy for teams already using Microsoft 365 and Teams
  • + Good fit for internal and external appointment scenarios with straightforward configuration

Cons

  • Limited advanced customization and workflow automation compared to dedicated scheduling platforms
  • Payments, marketing, and deep CRM integrations are less robust than specialist tools
  • Branding and booking-page flexibility can feel constrained for customer-facing use cases