How do I set up an automation workflow tool for sending check-in instructions and guest reminders?

Here’s a practical way to set up an automation workflow for sending check-in instructions and guest reminders.

1) Choose your tool

Pick an automation platform that can connect your booking system, calendar, email, SMS, and messaging apps. Common options:

• Zapier — easiest for simple automations
• Make (Integromat) — more flexible, visual workflows
• n8n — self-hosted, more customizable
• Airbnb/Booking platform automations — if your property management system already includes messaging

If you use a PMS/channel manager like Hostaway, Guesty, Lodgify, OwnerRez, check whether it already has built-in scheduled guest messaging. That’s often the simplest choice.

2) Define your trigger

Your workflow should start from a clear event, such as:

• New reservation created
• Booking confirmed
• Check-in date is 7 days away
• Check-in date is 1 day away
• Guest is marked as “arrived”

Example:

• Trigger: Reservation confirmed in your booking system
• Then: Add guest to a sequence of scheduled messages

3) Create your message sequence

A typical guest communication flow:

Immediately after booking

Send:

• A thank-you message
• Property basics
• What happens next
• Link to house rules or guest guide

7 days before check-in

Send:

• Arrival overview
• Address and parking info
• Arrival time reminders
• Optional upsell info like early check-in

1 day before check-in

Send:

• Check-in instructions
• Smart lock code or key pickup details
• Wi-Fi info
• Emergency contact

Day of check-in

Send:

• Welcome message
• Quick reminder of access steps
• Ask them to message if they have issues

Day before checkout

Send:

• Checkout time
• Checkout checklist
• Reminder about keys, trash, and dishes

After checkout

Send:

• Thank you message
• Review request
• Feedback form

4) Personalize the messages

Use variables from your booking data:

• Guest name
• Check-in date
• Property name
• Address
• Door code
• Wi-Fi password
• Parking instructions

Example:

Hi {{guest_first_name}}, your check-in at {{property_name}} is tomorrow. Your access code is {{door_code}}. Full instructions are here: {{guide_link}}

5) Add conditions and filters

To avoid sending the wrong messages, set rules such as:

• Only send if booking is confirmed
• Only send if arrival date is within a certain range
• Skip messages if reservation is canceled
• Send different instructions for direct bookings vs OTA bookings
• Send SMS only if phone number is available

6) Connect your communication channels

Decide where messages go:

• Email for detailed instructions
• SMS for urgent reminders
• WhatsApp for international guests if allowed
• In-app messaging for booking platforms

A good pattern is:

• Email = full details
• SMS = short reminder with link

7) Store your content in one place

Keep your check-in guide in:

• Google Docs
• Notion
• PDF guidebook
• Guest portal / digital welcome book

Then have your automation send a link instead of rewriting the full instructions each time.

8) Test before going live

Test with:

• A dummy reservation
• A friend’s email/phone
• A future check-in date

Check:

• Message timing
• Variables populate correctly
• Links work
• No duplicate messages are sent

9) Monitor and improve

Track:

• Open rates
• Response rates
• Guest questions
• Failed sends
• Which messages reduce support requests

Then refine the wording and timing.

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Simple example workflow

Trigger: Booking confirmed
Action 1: Create guest record in CRM
Action 2: Send welcome email immediately
Action 3: Wait until 2 days before check-in
Action 4: Send check-in instructions by email/SMS
Action 5: Wait until checkout day
Action 6: Send checkout reminder
Action 7: Wait 1 day after checkout
Action 8: Send review request

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Recommended setup for most hosts

If you want something straightforward:

• Use Hostaway/Guesty/Lodgify for booking data
• Use Zapier or Make for extra logic
• Use Twilio for SMS
• Use Gmail/SendGrid for email
• Store guide content in Notion or Google Docs

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If you want, I can also give you:

1. a step-by-step Zapier setup,
2. a Make.com scenario, or
3. a ready-to-use guest message template sequence.