Home / Shortlists / Best Scheduling Software for Contractors (2026)
Best Scheduling Software for Contractors (2026)
We compared the best scheduling software for contractors in 2026 - 4 tools that book estimate calls, install windows and deposits without phone tag. Every price below comes from each vendor's official pricing page, checked in October 2026.
Prices last re-checked 2026-10-12. Numbers are read from each vendor's own pricing page; any exception is flagged under "What to watch".
Which one should you pick?
- Pick Square Appointments if you are taking bookings and deposits. Visit Square Appointments
- Pick Cal.com if you are booking estimate calls. Visit Cal.com
- Pick Calendly if you need the best per-seat tool for a small crew. Visit Calendly
- Pick Acuity Scheduling if you need appointment-style services. Visit Acuity Scheduling
Some buttons are affiliate links — how this works.
The short answer
Short answer: Best for taking bookings and deposits: Square Appointments Square Free is $0/mo per location and you pay processing fees only when you take a payment, and Square Plus at $49/mo per location adds 500 marketing texts a month. Acuity Scheduling Starter also lists payment processing, at $20/mo.
| Tool | Entry price | Best for |
|---|---|---|
| Square Free | $0/mo | $0/mo per location. No monthly subscription cost - you only pay processing fees |
| Square Plus | $49/mo | $49/mo per location. Free 30-day trial. 500 marketing texts/mo per account, then |
| Square Premium | $149/mo | $149/mo per location. Free 30-day trial. Lowest processing fees. 2,500 marketing |
Prices checked 2026-10-12.
Best for taking bookings and deposits: Square Appointments
Square Free is $0/mo per location and you pay processing fees only when you take a payment, and Square Plus at $49/mo per location adds 500 marketing texts a month. Acuity Scheduling Starter also lists payment processing, at $20/mo.
See Square Appointments pricingBest for booking estimate calls: Cal.com
Cal.com Free is $0/mo for 1 user with unlimited event types and unlimited bookings - a contractor can offer a short estimate call and a full-day install as separate booking types on day one. Teams at $12/mo billed annually adds routing forms and round-robin.
See Cal.com pricingBest per-seat tool for a small crew: Calendly
Calendly Standard is $12/mo per seat - unlimited event types and multiple calendars for a crew that books across two or three calendars, while Free stays at $0/mo with 1 event type and unlimited bookings.
See Calendly pricingBest for appointment-style services: Acuity Scheduling
Acuity Scheduling Starter is $20/mo for 1 calendar with unlimited appointments, 100 SMS credits a month and payment processing - for a contractor selling fixed service windows with deposits.
See Acuity Scheduling pricingThe prices, plan by plan
Square Appointments
Square Appointments is $0/mo per location on Square Free, then $49/mo per location on Square Plus and $149/mo per location on Square Premium. Card processing is billed separately on every plan, and Square Plus and Square Premium each include a free 30-day trial.
| Plan | Price | What you get |
|---|---|---|
| Square Free | $0/mo | $0/mo per location. No monthly subscription cost - you only pay processing fees when you take a payment. No text-message marketing. 2.5% gift card load fee. |
| Square Plus | $49/mo | $49/mo per location. Free 30-day trial. 500 marketing texts/mo per account, then 3 cents per text. 2.5% gift card load fee. |
| Square Premium | $149/mo | $149/mo per location. Free 30-day trial. Lowest processing fees. 2,500 marketing texts/mo per account, then 1.5 cents per text. 0% gift card load fee. |
Prices checked 2026-10-12.
What to watch: Square prices per location and charges card processing on top of every plan - the monthly fee is not the whole cost. The marketing-text allowances are per account, not per location, and Square Free includes no text-message marketing.
Source: https://squareup.com/us/en/appointments/pricing, read 2026-10-19.
See Square Appointments pricingCal.com
Cal.com is free for one user. Teams is $12 per user/month and Organizations is $28 per user/month, both labeled YEARLY with a Save 25% badge. The page does not print a month-to-month price. Both paid plans say 14-day free trial. Enterprise is custom and the page says annual pricing.
| Plan | Price | What you get |
|---|---|---|
| Free | $0/mo (no annual discount published) | 1 user, unlimited event types, unlimited bookings, calendar connections |
| Teams | $12/mo billed annually | Per user. Labeled YEARLY at $12 per user/month with a Save 25% badge. The month-to-month price is not printed. Round-robin, collective events, routing forms, and a 14-day free trial. |
| Organizations | $28/mo billed annually | Per user. Labeled YEARLY at $28 per user/month with a Save 25% badge. The month-to-month price is not printed. Sub-teams, SAML SSO, managed event types, and a 14-day free trial. |
What to watch: Cal.com's free tier is one user but unlimited event types, which is more generous than Calendly's free tier. On 2026-10-11 the paid cards were labeled YEARLY and carried a Save 25% badge, and the page did not print a month-to-month price, so that column says not printed. Self-hosting has no licence fee, but the server bill is yours and is not in the table.
Source: https://cal.com/pricing, read 2026-10-19.
See Cal.com pricingCalendly
Calendly Standard is $10/seat yearly ($12 monthly) and Teams is $16 ($20); Notetaker and Callie make those $18 and $24 yearly ($24 and $32). Enterprise starts at $15,000 a year, from 50 seats. The Teams card's Popular plan badge is Calendly's, not a customer count.
| Plan | Price | What you get |
|---|---|---|
| Free | $0/mo (no annual discount published) | 1 user, 1 event type, 1 calendar connection, unlimited bookings |
| Standard | $12/mo, or $10/mo billed annually | Per seat. Unlimited event types and multiple calendars. The yearly card says save 17%. |
| Standard Plus | $24/mo, or $18/mo billed annually | Per seat. The Add Notetaker and Callie price. The base Standard card says Notetaker is not included. The yearly price says save 25%. |
| Teams | $20/mo, or $16/mo billed annually | Per seat. Round-robin, routing, and Salesforce. The card carries Calendly's own Popular plan badge. This page does not treat that badge as a count of customers. The yearly card says save 20%. |
| Teams Plus | $32/mo, or $24/mo billed annually | Per seat. The Add Notetaker and Callie price on Teams. The page says Teams Plus adds Notetaker. The yearly price says save 25%. |
| Enterprise | custom quote | Starts at $15,000 a year and starts at 50 seats. SSO, SCIM, audit logs, and dedicated support. Not a per-seat rate. |
Prices checked 2026-10-12.
What to watch: Calendly prints the yearly per-seat rate by default. The month-to-month rates and the Notetaker prices are in the same page's plan data, which is what the billing toggle and the Add Notetaker and Callie control use. The free plan is one event type and one calendar connection. The Teams card carries Calendly's own Popular plan badge. This page does not treat that badge as a count of customers.
Source: https://calendly.com/pricing, read 2026-10-12.
See Calendly pricingAcuity Scheduling
Acuity Scheduling is $20 a month on Starter, $34 on Standard and $61 on Premium, or $16, $27 and $49 a month billed annually, per account.
| Plan | Price | What you get |
|---|---|---|
| Starter | $20/mo, or $16/mo billed annually | 1 calendar, unlimited appointments, 100 SMS credits/mo, payment processing |
| Standard | $34/mo, or $27/mo billed annually | 6 calendars, 500 SMS credits/mo, coupons, gift certificates, add-ons |
| Premium | $61/mo, or $49/mo billed annually | 36 calendars, 1,500 SMS credits/mo, custom packages, advanced reporting |
Prices checked 2026-10-12.
What to watch: Acuity prices per account rather than per seat, so a team of five pays the same as a team of one - the opposite of Calendly and Cal.com. That makes it cheaper for teams and more expensive for a solo operator.
Source: https://acuityscheduling.com/pricing, read 2026-10-12.
See Acuity Scheduling pricingQuestions people ask
What is the best scheduling software for contractors?
Square Appointments is the best starting point for a contractor who wants bookings and card payments on one bill: Square Free is $0/mo per location and you pay processing fees only when you take a payment, and Square Plus at $49/mo per location adds 500 marketing texts a month.
What is the cheapest option here?
Square Appointments Free is $0/mo per location - the cheapest way to take bookings and deposits without a monthly subscription, with processing fees only when a customer pays.
When does Cal.com beat Calendly for a contractor?
Cal.com Free is $0/mo for 1 user with unlimited event types and unlimited bookings - a contractor can offer separate booking types for estimates and installs on day one, while Calendly Free is 1 user with 1 event type.
What does a crew pay per seat?
Calendly Standard is $12/mo per seat, or $10/mo billed annually - unlimited event types and multiple calendars for a crew that books across two or three calendars.
When is Acuity Scheduling the better fit?
Acuity Scheduling Starter is $20/mo for 1 calendar with unlimited appointments, 100 SMS credits a month and payment processing - a better fit than the per-seat tools for a contractor selling fixed service windows.
Some links on this page are affiliate links. If you buy through one we may earn a commission at no extra cost to you. We do not accept payment for placement, and the price tables are generated from the same dataset we re-check weekly. Full disclosure. How we check prices.