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Square Appointments vs Microsoft Bookings Comparison (2026)

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Square Appointments

Microsoft Bookings

Overview

Square Appointments is an all-in-one scheduling POS for booking, payments, and team management.

Microsoft Bookings is an online appointment booking and scheduling tool for small businesses, available as part of Microsoft 365 for Business subscriptions. Clients can book the time and service they need, get a confirmation email and calendar invitation, reschedule or cancel if they must.

Platforms supported

Web-based
iPhone app
Android app
Windows Phone app

Typical customers

Freelancers
Small businesses
Mid size businesses
Large enterprises

Customer support

Phone
Online
Knowledge base
Video tutorials

view more detailsview details

Platforms supported

Web-based
iPhone app
Android app
Windows Phone app

Typical customers

Freelancers
Small businesses
Mid size businesses
Large enterprises

Customer support

Phone
Online
Knowledge base
Video tutorials

view more detailsview details

Video & Screenshots

Pricing

Starting from

Per month

Free trial available
Credit cardless trial
Free account
Subscription based

Starting from

/user

Per month

Free trial available
Credit cardless trial
Free account
Subscription based

User reviews

4.5

263

177

Value for money

Ease of use

Features

Customer support

71%

would recommend this app

4.4

170

Value for money

Ease of use

Features

Customer support

77%

would recommend this app

Pros

“We needed more flexibility around trip types, availability, booking logistics, and managing the unique scheduling needs of charter customers.”

Bree B.

Administrative Assistant

“It worked well for scheduling trips, managing customer information, and keeping our calendar up to date.”

Bree B.

Administrative Assistant

“As our charter business grew, Square Appointments started to feel more like a general appointment-scheduling tool than something designed specifically for fishing charters.”

Bree B.

Administrative Assistant

Pros

“It simplifies appointment scheduling, reduces manual work, and keeps everything organized by syncing with Outlook and Microsoft 365. Once it's set up, it's easy to use for both staff and customers. While there are a few limitations with customization and the initial learning curve, it's a dependable scheduling solution that has saved me a lot of time.”

Jonathan K.

Chief Marketing Officer

“Customers can book available time slots online, automatic confirmation and reminder emails reduce no-shows, and everything stays synced with my Outlook calendar.”

Jonathan K.

Chief Marketing Officer

“It simplifies appointment scheduling by automating bookings, confirmations, reminders, and calendar management.”

Kate L.

Sales

Cons

“There can also be occasional glitches with calendar syncing or notifications, which can be frustrating when you rely on it for day-to-day appointment management.”

Nikki C.

OFFICE MANAGER

“The biggest downside is that some of the more advanced features can feel limited, especially when managing multiple staff members or more complex scheduling needs.”

Nikki C.

OFFICE MANAGER

“There isn’t anything that stands out that I did not like about Square Appointments. If I had to choose something it would be the lack of branding options.”

Cami B.

Owner

Cons

“Customer Support can be limited unless you have a higher-tier Microsoft support plan.”

Josh D.

IT Support Engineer

“I also had trouble getting the Online Chat option to work through my website and enabling the Booking option through it.”

John W.

Owner, Designer

“It cannot work with google software, so it has to be microsoft stack like outlook and outlook for web”

Ray W.

Senior Consultant