Scheduling · Head-to-head
Calendly vs Square Appointments vs Setmore: which fits a small business?
Square Appointments wins for businesses that take payment at the appointment (free for a solo pro, native card processing and deposits). Calendly wins for booking meetings, demos and calls (the most polished calendar-scheduling experience). Setmore wins on price for a small team, free for up to 4 users, then $5/user/month. They are three different jobs, so the answer is driven by whether you sell time slots, meetings, or appointments with payment.
Updated August 2026 · Reviewed by the SMB Stack Brief desk
| Calendly | Square Appointments | Setmore | |
|---|---|---|---|
| Free tier | 1 event type | Solo pro | Up to 4 users |
| Entry paid | $10/seat/mo (Standard, annual) | Plus/Premium (see site) | $5/user/mo (annual) |
| Team tier | $16/seat/mo (Teams, annual) | Premium | $5/user/mo |
| Payments | Add-on / integrations | Native (Square) | Native |
| Deposits / card on file | Via integrations | Yes | Yes (Pro) |
| Best job | Meetings, calls, demos | Appointments with payment | Cheap multi-staff calendar |
Calendly
Calendly is meeting-scheduling first: share a link, invitees pick a slot, it lands on your calendar. The free plan covers one event type; Standard is $10/seat/month and Teams $16/seat/month billed annually ($12 and $20 billed monthly), and Enterprise starts around $15k/year. Payments come through integrations rather than natively, which is the main gap for appointment-and-pay businesses.
Square Appointments
Square Appointments is booking bolted onto Square's point-of-sale, so payments, deposits and card-on-file are native. A solo operator can use it free (you still pay standard Square card fees); Plus and Premium are paid monthly tiers for multi-staff and advanced rules, Square does not publish a flat headline monthly figure on the page we checked, so confirm the current rate on their site.
Setmore
Setmore is the value pick for a small team: free for up to 4 users, then Pro at $5/user/month billed annually, with SMS reminders, two-way calendar sync and native payments on the paid tier. It is the cheapest way to give several staff their own bookable calendars.
NoShowLine, if no-shows are the whole problem
None of the three above is built purely around no-show reduction, they are general booking tools that happen to send reminders. If deposits and confirmations are the entire reason you are shopping, NoShowLine ($149/mo) is built narrowly for exactly that in clinics: WhatsApp/SMS confirmations paired with deposit holds. It is not a general-purpose replacement for Calendly, Square or Setmore, so weigh it specifically against your no-show cost, not as a fourth all-rounder.
Primary sources
- Calendly pricing, Square Appointments pricing, Setmore pricing, all verified August 2026.