Calendly vs Square Appointments Comparison 2026
Both cover scheduling & booking. Here is what separates them on price, billing, what you can take with you, and coverage.
A booking page that reads your own calendar
Booking and payments in one account
At a glance
- Calendly starts cheaper, at $10.
- Both have a genuinely free tier.
Side by side
Calendly | Square Appointments | |
|---|---|---|
| Starting price (they differ) | From $10 | From $49 |
| Pricing model | Free plan, paid tiers | Free plan, paid tiers |
| Free tier | Yes | Yes |
| Billing | Not stated | Monthly or annual |
| Free trial (they differ) | 14 days | 30 days |
| API | Yes |
Calendly
A booking page that reads your own calendar
Calendly publishes the times you are genuinely free and lets somebody claim one, which settles in a click what usually takes three emails. Buffers, round robin and paid bookings are there when the calls start earning. The free plan allows one event type, so anybody running a coaching call and a sponsor call from the same calendar pays.
Our note
The one to buy when a bad calendar is costing you calls. Start on Standard rather than free: the second event type is what everybody needs by the second week.
Only on this side
- Covers courses & coaching
Square Appointments
Booking and payments in one account
Square Appointments runs a booking site, staff calendars and reminders, and takes the payment through Square rather than through a separate processor. The free plan covers one location with no monthly fee at all, and the processing rate is where Square earns instead. Paying lowers that rate and adds the scheduling controls a team needs. Anybody who only wants a calendar link and never takes a payment is paying attention to the wrong half of this product.
Ratings are the average of reviews readers left. The facts are stated by each tool’s own listing and are not verified by CloutStack. How we make money.