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Calendars · head to head

Outlook Calendar vs Square Appointments

Outlook Calendar logo

Outlook Calendar

Calendars

Professional calendar management for Microsoft 365

From
Free
Rated
-
Full reviewWebsite
Square Appointments logo

Square Appointments

Scheduling

Free scheduling for beauty businesses

From
On request
Rated
-
Full reviewWebsite

The short version

  • Only Outlook Calendar has a free tier, so it costs nothing to try first.
  • Each has a real cost: Outlook Calendar offline support limited to only past 30 days of events, older events unavailable; Square Appointments the free plan is aimed at solo professionals; booking across multiple staff requires the paid Plus plan
  • They diverge on capability: Outlook Calendar covers Meeting scheduling, Square Appointments covers Online booking.
  • Prices and features above were last checked on 30 August 2026.

Where they differ

Only the attributes on which Outlook Calendar and Square Appointments actually diverge.

Attributes where Outlook Calendar and Square Appointments differ
AttributeOutlook CalendarSquare Appointments
Starting priceFreeOn request
Pricing modelUnknownusage-based
Free tierYesNo
PlatformsWeb, Windows, macOS, iOS, AndroidWeb, Ios, Android
CategoryCalendarsScheduling
Founded19752009

Identical on both: user rating (Not yet rated).

What each one covers

Drawn from each product's published feature list. An absence here means we hold no record of it - not that the product lacks it.

Only in Outlook Calendar

  • Meeting scheduling
  • Shared calendars
  • Room booking
  • Availability sharing
  • Recurring events
  • Microsoft Teams
  • OneDrive
  • SharePoint

Only in Square Appointments

  • Online booking
  • Client management
  • Point of sale
  • Payment processing
  • Automated reminders
  • Instagram booking
  • Google booking
  • Mobile app

Both cover

  • Web support

What people use each for

The jobs each tool is most often brought in to do.

Outlook Calendar

  • Schedulingnot Square Appointments
  • Appointment bookingnot Square Appointments
  • Time trackingnot Square Appointments
  • Resource managementnot Square Appointments
  • Team coordinationnot Square Appointments

Square Appointments

  • Online appointment booking for salons, barbers and personal servicesnot Outlook Calendar
  • Taking card payments and deposits at the time of bookingnot Outlook Calendar
  • Managing staff calendars, waitlists and no-show policiesnot Outlook Calendar

Where each one falls short

Documented limitations, not opinions. Every one is a constraint you would hit in normal use.

Outlook Calendar

  • Offline support limited to only past 30 days of events, older events unavailable
  • Shared calendars and group calendars not available offline
  • Cached Exchange Mode issues can limit available offline data
  • Occasional sync conflicts when coming back online

Square Appointments

  • The free plan is aimed at solo professionals; booking across multiple staff requires the paid Plus plan
  • Cancellation policies, no-show fees and waitlists require the Plus plan
  • Resource management, service cost tracking and the future bookings report require the Premium plan
  • Custom processing rates are reserved for Square Pro, which is aimed at businesses processing over $250,000 a year
  • Card processing fees are charged on top of the plan fee on every tier including the free one

Pricing, plan by plan

Outlook Calendar

Free
  • FreeFree
    • Outlook.com email and calendar
    • 50MB attachment limit
    • 1GB cloud storage
  • Microsoft 365 Basic$19.99/year
    • Outlook with limited features
    • Cloud storage
  • Microsoft 365 Personal$99.99/year
    • Premium Outlook
    • Ad-free email
    • 100GB mailbox storage
  • Microsoft 365 Business Basic$6/month
    • Business-class email
    • 1TB cloud storage
    • Microsoft Teams

Square Appointments

On request
  • Solo Professional Plan$null/transaction
    • Processing fees apply
    • For solo professionals taking payments and managing schedules
    • Top appointments features
  • Plus Plan$null/transaction
    • Processing fees apply
    • Free trial available
    • For growing teams needing more advanced tools
  • Premium Plan$null/transaction
    • Processing fees apply
    • Free trial available
    • For large salons with complex staff management
  • Square Pro$null/month
    • Custom pricing for businesses processing over $250,000 annually
    • Hardware discounts
    • Onboarding support

Which should you pick?

Choose Outlook Calendar if

  • You need meeting scheduling.
  • You want to start without paying.
  • You work on Web, Windows, macOS, iOS, Android.
  • You also want shared calendars.
Outlook Calendar review

Choose Square Appointments if

  • You need online booking.
  • You work on Web, Ios, Android.
  • You also want client management.
Square Appointments review

Questions people ask

Is Outlook Calendar or Square Appointments better?
Neither clearly leads. Outlook Calendar starts at Free and Square Appointments at On request, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Outlook Calendar or Square Appointments?
Outlook Calendar has a free tier; the other does not. Paid plans start at Free for Outlook Calendar and On request for Square Appointments.
Does Outlook Calendar or Square Appointments run on more platforms?
Outlook Calendar runs on Web, Windows, macOS, iOS, Android. Square Appointments runs on Web, Ios, Android.
Can I use Outlook Calendar for free?
Yes. Outlook Calendar has a free tier, so you can try it without paying. Square Appointments starts at On request.
What is Outlook Calendar best used for?
Outlook Calendar is most often used for scheduling, appointment booking, time tracking, resource management. Of those, scheduling and appointment booking are not what Square Appointments is typically brought in for.
What can Outlook Calendar do that Square Appointments cannot?
Outlook Calendar covers Meeting scheduling, Shared calendars, Room booking, Availability sharing. Square Appointments covers Online booking, Client management, Point of sale, Payment processing. Both handle Web support.

Answered from the vendors’ own pages

Outlook Calendar: Is Outlook Calendar free?

Outlook.com with calendar is free via a Microsoft account. Outlook Calendar also comes with Microsoft 365 Personal ($99.99/year), Family ($129.99/year), or Business plans starting at $6/user/month.

Source
Square Appointments: How much do Square Appointments plans cost?

Square Appointments pricing is based on processing fees rather than monthly subscription fees. Specific percentages are not listed online. The Solo Professional, Plus, and Premium plans all charge processing fees on transactions. For businesses processing over $250,000 annually, Square Pro offers custom pricing including hardware discounts, onboarding support, and account management.

Source
Outlook Calendar: Does Outlook Calendar work offline?

Outlook Calendar has limited offline support. New Outlook caches only the past 30 days of calendar items. Shared calendars and group calendars are not supported offline. Changes sync when you reconnect.

Source
Square Appointments: Is there a free trial for Square Appointments?

Yes, the Plus and Premium plans offer free trials for an unspecified number of days. The Solo Professional plan does not appear to offer a trial period.

Source
Outlook Calendar: What platforms does Outlook Calendar support?

Outlook Calendar is available on Windows (desktop and web), macOS (desktop and web), iOS, and Android. Real-time synchronization works across all devices.

Source
Square Appointments: What features does the Premium plan add compared to Plus?

The Premium plan includes all Plus features plus Future Bookings Report for tracking upcoming appointments, Service Cost Tracking to monitor service profitability, and Resource Management for scheduling equipment and facilities across multiple staff members.

Source
Outlook Calendar: Does Outlook Calendar integrate with Slack?

Yes. Outlook Calendar integrates with Slack to sync your status and receive meeting notifications. You can RSVP to invites directly in Slack and join Microsoft Teams meetings from Slack reminders.

Source
Outlook Calendar: Can you share calendars and set delegate permissions?

Yes. Outlook Calendar supports calendar sharing with delegate permissions, color categories for organization, and the Scheduling Assistant to view attendee availability for meeting times.

Source
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