Calendly vs Microsoft Bookings
Which scheduling & booking tool is right for you? Compare features, pricing, and user reviews to make the best choice.
Calendly
From $10Free plan
G2 4.7 · 2,648 reviewsIndividuals 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.
vs
Microsoft Bookings
From $7
G2 3.8 · 37 reviewsMicrosoft 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).
Side by side
 Calendly |  Microsoft Bookings | |
|---|---|---|
| Pricing | Free; paid from $10/seat/month (billed yearly) | From $7/user/month (via Microsoft 365 Business Basic) |
| G2 Rating | 4.7 (2,648 reviews) | 3.8 (37 reviews) |
| Best For | 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. | 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 and 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
Sarah Chen