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Calendly vs Microsoft Bookings
Priced at four team sizes, the features checked against both pricing pages.
Take Calendly if you want the one everybody knows, a free plan that works and booking sales calls. Take Microsoft Bookings if you want already in a suite you pay for and the one everybody knows. Calendly is cheaper at a small user count and Microsoft Bookings is cheaper by 2 users, so the answer changes with your size.
What each one actually costs
The real monthly figure at four team sizes with the add-ons each platform forces on you included, from the same engine the shortlist quiz uses. The cheaper of the two is marked on every row.
| Calendly | Microsoft Bookings | Difference | |
|---|---|---|---|
| 1 users | $0 | $8.40 | $8.40 |
| 2 users | $24 | $16.80 | $7.20 |
| 5 users | $60 | $42 | $18 |
| 10 users | $120 | $84 | $36 |
What is actually different
- Calendly lists AI features, embedding on your site, group bookings and classes, intake questions at booking, an API and integrations, a mobile app, taking payment at booking, round-robin across a team, routing forms and follow-up workflows where Microsoft Bookings does not, which is their own wording rather than something we verified.
- Microsoft Bookings lists SMS reminders where Calendly does not, which is their own wording rather than something we verified.
No verdict from me yet
I have not used Calendly or Microsoft Bookings on camera, so everything on this page comes from their own pricing pages, re-read weekly, and nothing from my own experience. When I review either, it will be here.
Before you sign up to either
| Calendly | Microsoft Bookings | |
|---|---|---|
| Free trial | 14 days | 30 days |
| Free plan | None | None |
| Contract | Monthly or annual per seat; Enterprise is annual only | Annual commitment (paid yearly or monthly) that auto-renews, or a monthly subscription at 20% more that can be cancelled any time |
| Payment fee | None on top | None on top |
Reading further
The full price ladder, every plan and the add-ons charged on top are on each platform's own page. If neither of these two is quite it, each page also has the alternatives ranked against it.
People search for this comparison as: calendly vs bookings, calendly vs microsoft bookings, microsoft bookings vs calendly, microsoft bookings vs calendly reddit.
Questions people ask about these two
Is Calendly or Microsoft Bookings cheaper?
Calendly is cheaper at a small user count and Microsoft Bookings is cheaper by 2 users, so the answer changes with your size.
How much does Calendly cost a month?
Calendly is free at 1 user, $24 a month at 2 users and $120 at 10 users, read off their own pricing page and re-checked every week.
How much does Microsoft Bookings cost a month?
Microsoft Bookings is $8.40 a month at 1 user and $84 at 10 users, read off their own pricing page and re-checked every week.
Does Calendly or Microsoft Bookings have a free trial?
Calendly publishes a 14-day free trial and a Free plan at $0. Microsoft Bookings publishes a 30-day free trial.
Make a third option? If you make scheduling and appointment booking tools and it is missing from this list, ask to be shortlisted. Listings are free and cannot be bought.
Neither, or not sure?
A head to head only helps once you have picked the two. The shortlist asks 6 questions about what people book with you and how many calendars there are, and gives you four picks priced at your own team size, from all 17.
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