One of the most challenging parts of a business is managing time with prospects and existing customers. Efficient or inefficient appointment scheduling directly impacts sales conversions, marketing campaign success, and customer retention.
Scheduling appointments with new and existing clients and managing time effectively are challenging. Sales teams lose valuable opportunities when prospects abandon due to complex booking processes. The marketing team’s efforts don’t yield expected results without seamless calendar integration. Manual coordination drains productivity and costs the business.
To mitigate these challenges and manage appointments, businesses often use a scheduling app. There are so many in the market, but the two that lead the market are there is an ongoing debate between MS Bookings and Calendly.
These two platforms share similar intent but differ significantly in features and pricing. This is what has sparked the debate – Microsoft Bookings vs Calendly, with each offering distinct advantages for different business scenarios.
This comprehensive comparison examines both platforms specifically from a Dynamics 365 user’s perspective, helping you determine which scheduling tool aligns with your operational needs, budget constraints, and CRM integration requirements.
Microsoft Bookings
Microsoft Bookings is an appointment scheduling app and a part of Microsoft 365. With its easy-to-use interface, you can use it to manage appointments and schedules. It becomes easy for customers to book, reschedule or cancel meetings.
MS booking is suitable for small-sized businesses. It is also integrable with Outlook and other private calendars of your website.
Its core capabilities include:
- Booking pages: Customizable scheduling interfaces that reflect your brand.
- Staff assignment: Automatic resource allocation based on availability and expertise.
- Availability and working hours: Configurable time slots with buffer periods and booking limits.
- Outlook and Teams integration: Seamless synchronization with existing Microsoft calendars and virtual meeting platforms.
As discussed above, it fits the requirements of small businesses but won’t be able to fulfill the demands of enterprises. So, if you have a growing business, it might not be the best choice for your business.
However, when evaluating the MS Bookings vs Calendly debate, one thing you must consider. It is that Microsoft Bookings shines brightest, in Microsoft-centric environments where teams already leverage Outlook, Teams, and other 365 applications for daily operations.
Calendly
Calendly is software for booking appointments and managing schedules. It is popular for its meeting scheduling features, which lets customers select a time slot, to book their appointment.
Unlike Microsoft Bookings, Calendly is a standalone solution that integrates with a wide range of tools and platforms, making it a versatile choice for diverse technology stacks.
Other than the meetings scheduling, Calendly offers many customizable features that make it suitable for businesses of varied scopes and sizes.
Key capabilities include:
- Booking links: Shareable URLs that embed into emails, websites, and social media.
- Time zone detection: Automatic adjustment for global meeting coordination.
- Team scheduling and routing: Round-robin, collective, and priority-based assignment options.
- Integrations with multiple platforms: Native connections to Salesforce, HubSpot, Zoom, Google Calendar, and hundreds of other tools.
Calendly, as a third-party app, offers greater flexibility. While you may need to pay for third-party extensions to integrate it with your CRM, it will also help you avoid single-ecosystem limitations.
In the Calendly vs Microsoft Bookings comparison, Calendly excels for organizations requiring cross-platform compatibility, advanced routing logic, and extensive third-party integrations beyond the Microsoft environment.
Microsoft Bookings vs Calendly: Pricing Comparison
This is one of the most important differences between the two. Calendly and Microsoft Bookings have very distinct pricing models, which play a major role in the decision.
Microsoft Bookings
MS Bookings isn’t sold as an individual product. It is an additional tool included at no cost with some Office 365 and Microsoft 365 subscription plans, such as Business Basic, Business Standard, Team Essentials, and Premium.
Calendly
Calendly offers many plans for the team to choose from based on their requirements. It starts free with basic functionality for personal use and scales up upto enterprise-level, starting at $15k annually. The features and functionality available depend on the plan you choose.
Feature Comparison: Microsoft Bookings vs Calendly
This section will help you get a better understanding of how the two Microsoft Bookings and Calendly compare and contrast by comparing their features side-by-side.
Scheduling and Availability Management
Microsoft Bookings synchronizes directly with Outlook calendars, automatically blocking unavailable time slots based on existing appointments. Staff members maintain their regular Outlook schedules, and Bookings reflects real-time availability without manual updates. However, customization options remain limited to basic working hours and service duration settings.
Calendly provides granular control over availability rules. Users can configure minimum scheduling notice periods, buffer times between meetings, daily meeting limits, and specific date overrides. Advanced features include secret event types, custom scheduling windows, and conditional logic based on invitee responses.
Microsoft Bookings prioritizes simplicity with Outlook-driven automation, while Calendly offers sophisticated controls for complex scheduling scenarios requiring precise availability management and meeting flow optimization.
Time Zone Handling
Microsoft Bookings uses Microsoft 365 timezone configurations, so users have to manually select their timezone when they are booking. This is good for single-timezone operations, but can cause some serious friction when working with international clients.
Calendly detects invitee time zones and displays available slots in their local time without any manual intervention. This eliminates the error opportunities when working with global teams and international clients and ensures easy coordination.
For global client bases, Calendly’s automatic detection proves superior. Microsoft Bookings works adequately when scheduling occurs primarily within consistent timezone regions or among Microsoft 365 users.
Integration and Ecosystem
Microsoft Bookings operates exclusively within the Microsoft 365 environment, offering native integration with Outlook, Teams, Exchange, and SharePoint. This ensures seamless data flow for organizations committed to Microsoft infrastructure but it also creates ecosystem dependency that limits external connectivity.
Calendly embraces cross-platform flexibility with 100+ native integrations spanning CRM systems (Salesforce, HubSpot), video conferencing (Zoom, Google Meet), payment processors (Stripe, PayPal), and marketing automation tools. However, many advanced integrations require paid Calendly plans and separate third-party subscription costs.
The Calendly vs Microsoft Bookings integration debate centers on priorities. Microsoft Bookings delivers frictionless Microsoft ecosystem harmony, while Calendly provides versatile connectivity across diverse technology stacks. You need to weigh ecosystem lock-in benefits against cross-platform operational requirements.
Ease of Use and Setup
Microsoft Bookings requires minimal setup for existing Microsoft 365 subscribers. It can be activated in minutes by connecting staff members’ Outlook calendars. The intuitive interface mirrors familiar Microsoft design patterns, reducing training time for teams already comfortable with Office applications.
Calendly demands more upfront configuration but offers users with extensive customization options. Initial setup requires the team to define availability rules, create event types, configure notifications, and establish integrations. While the learning curve is steeper, advanced users gain precise control over scheduling workflows.
When examining Microsoft Bookings and Calendly from a usability perspective, consider team technical proficiency and desired configuration depth versus implementation speed.
To summarize all of it:
| Feature | Microsoft Bookings | Calendly |
| Booking Pages | Basic customization with Microsoft branding | Advanced customization with white-label options |
| Availability Management | Syncs with Outlook calendars automatically | Connects to multiple calendar platforms |
| Team Scheduling | Staff assignment with skills-based routing | Round-robin, collective, and priority routing |
| Time Zone Handling | Manual timezone selection required | Automatic detection and conversion |
| Calendar Integrations | Native Microsoft 365 ecosystem only | Google, Outlook, iCloud, and others |
| CRM Integrations | Limited native CRM connectivity | Extensive integrations via third-party connectors |
Which One is The Best?
The best scheduling app for you would totally depend on your business requirements. Make a list of the features you seek and compare those within both apps. The next step would be price. For a small business, prices are going to matter a lot.
For MS Bookings, you have to be a Microsoft 365 user. If you have basic requirements like scheduling a meeting and managing schedules, MS Bookings might be the best choice for you.
You won’t have to pay extra for an app and can use it to better plan your days. But here, you have limited features and limited growth chances.
If you use any other platform, Calendly can be your tool. It is not platform specific and comes with a lot of features designed to make the meeting scheduling process easy for users.
But if businesses wish to use their CRM data while managing schedules, they have to pay extra to third-party extensions to integrate CRM into Calendly.
As you know, Calendly offers only limited functionalities in the free plan, you have to purchase a paid plan for business activities. Additionally, you also have to pay extra for the integration extensions.
Thus, you are paying at two places. Small businesses might find it costly as you have to pay extra over Calendly’s pricey-paid plans.
Bonus Suggestion for Dynamics 365 Users: Calendar 365
For organizations evaluating Microsoft Bookings vs Calendly while operating within Dynamics 365, Calendar 365 presents a purpose-built alternative. Developed for Dynamics 365 environments, this plugin eliminates the need for third-party scheduling tools and integration expenses.
Dynamics 365 Calendar centralizes appointment scheduling directly within your CRM interface, ensuring seamless access to customer data during booking processes. The plugin offers fully configurable calendar types tailored to CRM workflows:
- Resource Calendar: Manage staff availability and assignment
- Entity Calendar: Schedule activities linked to specific CRM records
- Customer Calendar: Provide client-facing booking portals
Unlike Calendly’s subscription model requiring separate integration costs, Calendar 365 requires no recurring third-party fees. The intuitive interface syncs seamlessly into the Dynamics 365 environment and functions similarly to standalone tools without the data silos or ecosystem fragmentation.
For Dynamics 365 users, Calendar 365 delivers comparable scheduling capabilities while maintaining unified CRM operations and cost efficiency.
Final Thoughts
The Microsoft Bookings vs Calendly decision ultimately depends on your organizational priorities and existing infrastructure. Microsoft Bookings excels for Microsoft 365-committed teams seeking straightforward scheduling with minimal setup, while Calendly serves businesses requiring cross-platform flexibility and advanced customization.
Evaluate your technology ecosystem first because native integrations reduce friction and costs. Assess scheduling complexity requirements against each platform’s capabilities. Finally, calculate total ownership costs, including subscriptions, integrations, and potential Dynamics 365 alternatives like Calendar 365.
The right scheduling tool streamlines operations, improves customer experience, and scales with your business growth. Choose the solution that aligns with your technical environment, budget constraints, and long-term operational strategy, rather than relying on feature lists alone.
Get the best of both worlds with Calendar 365, designed exclusively for Dynamics 365 users who demand seamless CRM integration without compromise.
