This is the first time I've seen Bookings, which appeared in my new Outlook. Honestly, I have no idea what it does or how it can help me. It looks like a slightly different way to book my appointments rather than from my calendar. I thought it was going to help integrate having multiple emails (and companies) in Outlook, attempting to combine them (and share, even if it shows other companies as "private meetings") so that I can share my calendar with outside parties. Further, I thought it would work like Calendly amongst my multiple emails/calendars so that I can send vendors/customers/employees my schedule by day, and it lists the times I (and others) are open for group meetings. I can't tell if it does any or none of these.
I would suggest Microsoft take more suggestions from the comments pages as mentioned above, and when new products are rolled out, feature them with an in-depth (video) presentation on the features and how they work with examples. That is what Todoist does, and it's very helpful.