Microsoft Bookings vs Calendly
A detailed, unbiased comparison to help you choose the right scheduling software for your needs. Updated for 2026.
Key Takeaways
- Microsoft Bookings excels at: Included with M365
- Calendly excels at: Works with any email
- Calendly wins 4 out of 6 categories
- Microsoft Bookings is best for: Microsoft 365 organizations
- Calendly is best for: Anyone wanting premium scheduling
Quick Overview
Microsoft Bookings
Microsoft Bookings is included with Microsoft 365. Best for organizations already in the Microsoft ecosystem.
Pros
- Included with M365
- Teams integration
- Outlook calendar sync
- Multi-staff support
- Virtual appointments
Cons
- Requires M365 subscription
- Limited outside Microsoft
- Basic customization
- Clunky interface
Calendly
Calendly is a standalone scheduling platform. Best for users wanting the best scheduling experience regardless of email provider.
Pros
- Works with any email
- Modern, clean interface
- Extensive integrations
- Good free plan
- Easy to use
Cons
- Extra cost on top of M365
- Less deep Microsoft integration
Feature-by-Feature Comparison
| Feature | MS Bookings | Calendly | Winner |
|---|---|---|---|
| Cost for M365 Users | Included | Additional | MS Bookings |
| User Experience | Dated | Excellent | Calendly |
| Teams Integration | Native | Via integration | MS Bookings |
| Non-Microsoft Calendars | Limited | Excellent | Calendly |
| Integrations | Microsoft only | Extensive | Calendly |
| Customization | Basic | Good | Calendly |
“After comparing Microsoft Bookings and Calendly, I found SchedulingKit offered a better balance of features and pricing for my business needs.”
Our Verdict
Use Microsoft Bookings if you're fully in the Microsoft ecosystem and want no extra cost. Use Calendly for a better experience and more flexibility. SchedulingKit works with both ecosystems at a better price.
Frequently Asked Questions
Is Microsoft Bookings or Calendly better for small businesses?
It depends on your specific needs. Microsoft Bookings is best for microsoft 365 organizations. Calendly is best for anyone wanting premium scheduling. Consider your budget, required features, and technical comfort level when choosing.
Which is more affordable, MS Bookings or Calendly?
Microsoft Bookings pricing: Included with Microsoft 365 Business. Calendly pricing: Free (1 event type) / $10-16/seat/month. Compare your expected usage and required features to determine the best value for your situation.
Can I switch from MS Bookings to Calendly?
Yes, you can switch between these platforms, though there's no direct migration tool. You'll need to recreate your event types, update booking links on your website and email signature, and reconnect calendar integrations. Plan for 1-2 hours of setup time.
What are the main differences between MS Bookings and Calendly?
The key differences are in their target users and feature focus. Microsoft Bookings's strengths include: Included with M365, Teams integration. Calendly's strengths include: Works with any email, Modern, clean interface. Review the comparison table above for a detailed breakdown.
Is there a better alternative to both MS Bookings and Calendly?
SchedulingKit offers a compelling alternative that combines the best features of both platforms. With a generous free tier and powerful features like automated reminders, intake forms, and team scheduling, it's worth considering if neither option fully meets your needs.
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