Calendly vs Square Appointments: Pricing and Ratings Compared (2026)
Entry prices and free plans as read on each vendor's pricing page, and user ratings as published on review sites, for Calendly and Square Appointments side by side. This page compares data; it is not a hands-on review.
On the data: On the data below, Calendly leads on higher user rating and lower entry price. We do not name an overall winner for this pair.
Short on time? Here's the quick answer
Based on published vendor pricing and features and on public review data, here's who should pick what:
Calendly
Scheduling automation platform
Best for you if:
- • You want easy to use
Square Appointments
Manage appointments, staff, and services with free online booking and scheduling software.
Best for you if:
- • You want booking software
| At a Glance | Calendly | Square Appointments |
|---|---|---|
Starts at | Free plan, paid from $10/mo, billed monthly Standard plan | Free plan, paid from $29/mo, billed monthly Plus plan |
Category | Meeting Scheduling Productivity | Meeting Scheduling CRM |
Rating | 4.7/5 Capterra 4.7 · G2 4.7 6,801 reviews | 4.5/5 Capterra 4.5 262 reviews |
Free plan | Yes | Yes |
Watch out for | Routing forms (directing invitees to the right person) require Teams plan at $16/seat/mo | n/a |
Choose Calendly or Square Appointments?
Choose Calendly if
- You want easy to use
- You want good calendar integrations
- Budget matters ($10/mo, billed monthly vs $29/mo, billed monthly)
Choose Square Appointments if
- You want booking software
- You want square integration
In-Depth Analysis
Calendly
Scheduling automation platform
Calendly is the scheduling standard but the free plan is crippled to one event type.
Watch out
Routing forms (directing invitees to the right person) require Teams plan at $16/seat/mo
Strengths
- Pro: Easy to use
- Pro: Good calendar integrations
- Pro: Team features
- Pro: Automated reminders
Weaknesses
- Con: Limited customization on free
- Con: Can get expensive for teams
- Con: Basic analytics
Key features
Square Appointments
Manage appointments, staff, and services with free online booking and scheduling software.
Square Appointments offers a generous Free tier for single-location businesses, making it highly accessible.
Strengths
- Pro: Booking software
- Pro: Square integration
- Pro: Fair pricing
- Pro: Good features
- Pro: Active development
Weaknesses
- Con: Square ecosystem
- Con: Per-staff pricing
- Con: Better alternatives exist
- Con: Feature gaps
- Con: Support varies
Key features
Plans and prices: Calendly vs Square Appointments
| Tool | Plans and prices | Source |
|---|---|---|
| Calendly |
| calendly.com/pricing read Oct 30, 2026 |
| Square Appointments |
| squareup.com/us/en/appointments/pricing read Oct 4, 2026 |
Prices as read on each vendor's own pricing page on the date shown. Plans are listed per tool and are not matched against the other tool's plans: a plan name or price in one column says nothing about the same row in the other. Details on Calendly pricing and Square Appointments pricing.
Key Takeaways
Calendly
- Higher user rating: 4.7/5 vs 4.5/5
- Lower entry price: $10/mo, billed monthly vs $29/mo, billed monthly
Square Appointments
- Choose if you want manage appointments, staff, and services with free online booking and scheduling software
What the data shows
On the data below, Calendly leads on higher user rating and lower entry price. We do not name an overall winner for this pair.
- Calendly has the higher user rating (4.7/5 from 6,801 reviews for Calendly, 4.5/5 from 262 reviews for Square Appointments).
- Calendly has the lower entry price: $10/mo, billed monthly (Standard) against $29/mo, billed monthly (Plus) for Square Appointments.
- Both have a free plan.
Criteria: user rating (only above 20 reviews on both sides, gap of 0.2 or more), entry price (only on the same billing basis), free plan. How we rate
Frequently Asked Questions
How do Calendly and Square Appointments compare in 2026?
On the data below, Calendly leads on higher user rating and lower entry price. We do not name an overall winner for this pair. Calendly has the higher user rating (4.7/5 from 6,801 reviews for Calendly, 4.5/5 from 262 reviews for Square Appointments). Calendly has the lower entry price: $10/mo, billed monthly (Standard) against $29/mo, billed monthly (Plus) for Square Appointments. Both have a free plan.
What are Calendly and Square Appointments used for?
Calendly: Scheduling automation platform. Square Appointments: Manage appointments, staff, and services with free online booking and scheduling software.
What does Calendly cost vs Square Appointments?
Calendly's cheapest paid plan is Standard at $10/mo, billed monthly; it also has a free plan. Square Appointments's cheapest paid plan is Plus at $29/mo, billed monthly; it also has a free plan. Prices read on the vendors' pricing pages, latest check Oct 30, 2026.
What's the main difference between Calendly and Square Appointments?
Calendly's main strength: easy to use. Square Appointments's main strength: booking software.