Head to head · US edition
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If your organization already pays for Microsoft 365 Business Basic or Standard, Bookings costs nothing extra. Calendly costs more but is easier to use and far more flexible.
Prices as ofUSD as published
Choose Calendly if
- You want a polished booking page and wide integrations
- You take payments through Stripe or PayPal
- You use Google Calendar or a mix of calendars
Choose Microsoft Bookings if
- You already have Microsoft 365 Business Basic or Standard
- Everyone works in Outlook and Teams
- Budget matters more than polish
Our verdict Microsoft-based organizations should try Bookings first because it's already paid for. Move to Calendly if the setup, customization or lack of payments gets in the way.
Side by side
| Detail | Calendly | Microsoft Bookings |
|---|---|---|
| Best for | Solo professionals, sales and recruiting teams booking meetings | Organizations already paying for Microsoft 365 |
| Free plan | Yes: 1 event type, 1 calendar | Included in Microsoft 365 Business Basic and Standard; not sold separately |
| Entry price | From $10 per seat/month (annual billing) | From $7 per user/month (annual billing) |
| Currency and tax | Prices in US dollars as published by the vendor. Sales tax may be added depending on your state. | Prices in US dollars as published by the vendor. Sales tax may be added depending on your state. |
| Payments | Stripe, PayPal | Limited |
| SMS reminders | Not checked | Not checked |
| HIPAA option | Not checked | Not checked |
| UK/EU data angle | Not checked | Not checked |
| Teams | Teams plan; routing | Staff calendars in Microsoft 365 |
| AI features | Notetaker and Callie AI (Plus plans) | Not checked |
| Marketplace | No | No |
| Open source / self-host | No | No |
| Video calls | Zoom, Teams, Meet | Microsoft Teams |
| Integrations | Google, Outlook and iCloud calendars; Zoom, Microsoft Teams and Google Meet; Salesforce; HubSpot; Stripe; PayPal; Zapier | Outlook, Microsoft Teams, Microsoft 365 |
| Third-party ratings | G2 4.7/5 (2,679 reviews); Capterra 4.7/5 (4,169 reviews) Third-party figures as listed around 19 October 2026; not our ratings | Not checked |
| Strengths |
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| Weaknesses |
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| Visit | Visit Calendly | Visit Microsoft Bookings |
Plans and prices
Calendly
| Plan | Annual billing (per month) | Monthly billing | Unit | Tax |
|---|---|---|---|---|
| Standard | $10 | $12 | per seat/month | Sales tax may apply |
| Teams | $16 | $20 | per seat/month | Sales tax may apply |
| Standard Plus (adds Notetaker and Callie AI) | $18 | Not captured | per seat/month | Sales tax may apply |
| Teams Plus (adds Notetaker and Callie AI) | $24 | Not captured | per seat/month | Sales tax may apply |
Microsoft Bookings
| Plan | Annual billing (per month) | Monthly billing | Unit | Tax |
|---|---|---|---|---|
| Microsoft 365 Business Basic (includes Bookings) | $7 | $8.40 | per user/month | Sales tax may apply |
| Microsoft 365 Business Standard (includes Bookings) | $14 | $16.80 | per user/month | Sales tax may apply |
What each costs for a team
| Tool | Free plan | 1 person | 3 people | 5 people | Basis |
|---|---|---|---|---|---|
| Calendly | Yes: 1 event type, 1 calendar | $10 Standard | $30 Standard | $50 Standard | billed annually |
| Microsoft Bookings | Included in Microsoft 365 Business Basic and Standard; not sold separately | $7 Microsoft 365 Business Basic (includes Bookings) | $21 Microsoft 365 Business Basic (includes Bookings) | $35 Microsoft 365 Business Basic (includes Bookings) | billed annually |
Monthly list price for the cheapest paid plan that covers that many people, calculated from published per-user, per-staff or per-calendar prices (arithmetic only, no discounts). Tools priced per location or per calendar cost the same within the plan's limits. Free plans may cover you instead; see each tool's limits.
Questions people ask
Which is cheaper, Calendly or Microsoft Bookings?
Calendly: From $10 per seat/month (annual billing). Microsoft Bookings: From $7 per user/month (annual billing). Check how each one charges (per seat, per calendar or per location) using the team cost table on this page.
Do Calendly and Microsoft Bookings have free plans?
Calendly: Yes: 1 event type, 1 calendar. Microsoft Bookings: Included in Microsoft 365 Business Basic and Standard; not sold separately.
Related
- Calendly vs Acuity Scheduling
- Calendly vs Cal.com
- SimplyBook.me vs Calendly
- The best Calendly alternatives (2026)
- Compare all 21 tools: prices and feature matrix
Full reviews: Calendly · Microsoft Bookings
Sources
Prices and features as recorded on November 2, 2026 from these pages (research pass 26 October to 2 November 2026). Prices change: check the vendor's page before you buy. Spotted something out of date? Tell us.