Try Microsoft Bookings first if your team already has suitable Microsoft 365 licences and mainly needs customers to book staff or services. Shortlist Calendly when you need scheduling across different calendar accounts, explicit round-robin distribution or a booking process tied to sales tools. Paying for another scheduler is worthwhile only if it solves a real gap.
Both products can put a booking link in front of a customer. The differences become clearer when you ask who receives the appointment, which calendars block the time and what happens before and after the meeting.
Table of Contents
The choices that matter
| Requirement | Calendly | Microsoft Bookings |
|---|---|---|
| Starting point | Standalone Free or paid account | Check your eligible Microsoft subscription |
| Basic free scheduling | One event type and one connected calendar | Access depends on the Microsoft licence and configuration |
| Team allocation | Teams includes round-robin scheduling | “Anyone” can assign an available staff member randomly |
| Likely first trial | Cross-calendar meeting and sales workflow | Shared staff and service booking page |
Product details are documented in Calendly’s plan comparison, Microsoft’s Bookings administration guide and the Bookings FAQ.
Check what you already pay for
Microsoft’s UK page lists Business Basic with Teams at £5.40 per user per month, paid yearly, excluding VAT. It is an automatically renewing annual subscription and includes Bookings. This is the price of a wider business suite, not a separate Bookings subscription. Microsoft 365 UK pricing.
If those licences are already part of your business, the additional subscription cost of using the included scheduler may be zero. If you use another office suite and would buy Microsoft 365 only for scheduling, include the full new licence cost. Those two starting positions lead to very different comparisons.
Do not assume any product called Microsoft 365 is sufficient. For the Bookings app in Teams, Microsoft’s requirements include Exchange Online, Bookings enabled by an administrator and an appropriate licence. Staff participating in Teams meetings also need licences that support Teams meeting scheduling. Bookings prerequisites.
Calendly charges for the hosts who need seats; invitees do not need a paid seat to book. Compare its monthly and annual options against the exact features required. A scheduler that your customers use is not normally priced simply by counting everyone who attends.
Connect the calendars that actually define availability
A booking link is only useful if it protects the correct time. List every calendar that can contain a conflict: employment, consultancy, a second business and personal commitments. Decide which calendars should block slots and where a confirmed meeting should be created.
Calendly Free allows one connection, while its paid scheduling plans list six. Standard also adds unlimited event types, reminders and integrations including Stripe and PayPal. Those are useful distinctions for someone offering several appointment lengths or paid consultations. Calendly scheduling features.
Microsoft Bookings is closely integrated with staff Microsoft 365 calendars and supports personal and shared booking pages. For a business with a common Microsoft environment, that can make a shared service schedule a sensible first trial. Check calendars and staff availability in the actual tenant rather than assuming every existing appointment will block booking correctly.
“Anyone available” is different from equal distribution
This difference matters for sales teams. Microsoft says that when “Anyone” is selected, available staff are assigned randomly. It does not guarantee equal distribution or a per-person assignment cap. Calendly places round-robin scheduling in its Teams plan. Microsoft’s staff-allocation explanation; Calendly Teams.
For an illustrative three-person consultancy, random allocation may be fine for routine support appointments: the objective is simply to offer the first convenient time. It may be unsuitable for distributing new sales leads when the team expects a particular allocation policy. That is a business-rule difference, not merely a preference for one interface.
Write the policy before choosing. Does the customer choose a named consultant? Should the next appointment go to whoever is free, whoever has the fewest bookings, or the owner of an existing account? Then check that exact behaviour in the relevant plan.
Rehearse the customer’s complete journey
Build one realistic appointment type and follow it from a phone. The test should begin where a customer encounters your business, rather than from the scheduler’s administration screen.
- Choose a slot. Check the displayed time zone, meeting duration, required information and instructions.
- Confirm the meeting. Verify which calendar receives it and that the joining link or physical location is clear.
- Move or cancel it. Check customer permissions, notice periods and which staff members are notified.
- Add a conflicting event. Confirm that availability changes on the public page.
- Follow the result into your other tools. Check any CRM update, payment or follow-up task that your process needs.
Bookings can display times in the visitor’s local time zone, depending on configuration. Its business hours and staff scheduling use the business time zone. Check a London appointment with an overseas visitor and a date after a clock change rather than assuming the displayed time is obvious. Bookings time-zone settings.
For alternative tools built around different appointment models, see our appointment scheduling software guide. If bookings must update customer records, our free CRM comparison helps clarify the other half of the process.
Plan for administration, not just the booking page
Ask who will own the schedule when a colleague leaves. Someone needs to remove staff, change working hours, update services and investigate customer complaints. Keep a short record of the account owner, connected calendars and external integrations.
Also decide what information the booking form needs. A name, contact address and concise appointment purpose may be enough. Sensitive case details are better considered separately from routine scheduling, with an appropriate process for access and storage.
Do not buy an annual plan before validating reminders, payment handling, staff assignment and cancellation behaviour. A feature with a familiar name may still require a different plan, an add-on or a configuration change.
The decision for a small business
Microsoft Bookings is the logical first trial for an eligible Microsoft 365 team offering a shared set of services. Calendly becomes compelling when multiple calendar connections, paid consultations or sales-routing requirements justify a separate subscription. Choose on the basis of a completed customer journey and an understood staff-allocation rule, then compare the annual cost of the exact configuration.
Checked 9 September 2026 against official documentation. Examples are illustrative.
