How to Automate Pre-Arrival Messages in Hostaway for Airbnb and Booking.com (2026)

Why Pre-Arrival Messages Are Your First Line of Defence Against Bad Reviews

Check-in day is the highest-friction moment of any STR stay. Guests are travelling, often tired, and arriving somewhere unfamiliar. If they can't find the lockbox code, can't connect to the WiFi, or don't know where to park — that frustration lands in your reviews, not just in a message thread.

The property managers who consistently hit 4.9★ don't have fewer guest questions. They've answered those questions before guests can ask them. A well-timed pre-arrival sequence does most of that automatically — no VA needed, no late-night reply required. Hostaway's triggered message automation makes this straightforward to configure. The challenge most operators run into isn't the technology — it's knowing exactly what to include in each message and when to send it.

The 3-Message Pre-Arrival Sequence

Message 1: At Booking (or 7 Days Before Check-In)

Send this immediately after the booking is confirmed. The guest just booked — they're engaged and they'll actually read what you send right now. Don't front-load logistics here. This message should confirm the dates and property name, set expectations for when they'll receive check-in details, and include one line about something to look forward to — the view, the pool, the location. Keep it under 150 words. Hosts who send a 600-word wall of text at booking signal that the property is high-maintenance before the guest has even arrived.

Message 2: 24 Hours Before Check-In (The Logistics Message)

This is where the practical information lives. Send it exactly 24 hours before check-in — not 5 days out, not the morning of. Twenty-four hours is close enough that guests are mentally preparing but not mid-journey. Include:

• Check-in procedure — step-by-step, with the lockbox or door code
• Parking instructions — exact location, any permit requirements
• WiFi name and password — put this high up, guests always want it first
• Property address — and any navigation notes (GPS often takes guests to the wrong entrance)
• Contact method — how to reach your guest messaging system if they hit an issue

Keep this under 300 words. Use line breaks and short sections. Guests read this on their phone while packing — dense paragraphs don't get read.

Message 3: 2 Hours Before Check-In (The Arrival Prompt)

Short. Warm. Practical. This message serves one purpose: confirming the guest knows exactly how to get in. Two to three sentences at most:

"You're almost here! Your door code is [CODE]. WiFi is [NETWORK] / [PASSWORD]. Message us if you hit any snags on arrival."

This message has the highest open rate of the three and reduces check-in-day support messages by roughly 40% for operators who weren't sending it before. It's not redundant — guests in travel mode often don't fully process the 24-hour message until they're standing at the door.

What Message Templates Can't Handle

A timed sequence eliminates predictable questions. It doesn't handle unpredictable ones — the guest who arrives early, the door code that isn't working, the question in Portuguese about whether there's a hairdryer.

That's where static automation breaks down. Hostaway's triggered messages are excellent for outbound sequences; they're not a replacement for real-time responses when guests need answers outside the script.

Guestar connects to your Hostaway account and handles the live follow-up — responding to guest messages in under 2 minutes, in 100+ languages, from your property knowledge base. When a guest replies to your 24-hour message asking about early check-in, or sends a check-in-day question in German, Guestar answers instantly without you needing to be available. Anything genuinely complex escalates to you rather than getting a wrong answer.

Together, triggered pre-arrival sequences and AI guest messaging cover the full check-in window — the planned questions and the unplanned ones. Operators running both consistently report fewer check-in-day messages, stronger Airbnb response rate scores, and fewer check-in complaints in their reviews.

FAQ

How many pre-arrival messages should I send in Hostaway?

Three is the standard that works for most STR operators: one at booking, one 24 hours before check-in, and one 2 hours before arrival. Some operators add a fourth message for long-stay guests — 7 days out with local recommendations — but for most properties, three messages covers the critical logistics without overwhelming the guest.

What's the most important thing to include in a Hostaway pre-arrival message?

The door code and WiFi password, in that order. These are the two things guests look for the moment they arrive, and not finding either of them quickly is responsible for a disproportionate share of check-in complaints and 3-star reviews. Put them near the top of your 24-hour message and repeat them in the 2-hour reminder.

Should pre-arrival messages be different for Airbnb and Booking.com guests?

The logistics content should be identical — same check-in steps, same codes. The tone can differ slightly. Airbnb guests tend to be comfortable with self-check-in; Booking.com guests, particularly international travellers, often expect more explicit step-by-step guidance. If your Hostaway setup allows platform-specific message variants, it's worth making the Booking.com version more detailed, especially for properties with complex access instructions.

Can Guestar handle pre-arrival guest messages in Hostaway?

Guestar handles the real-time follow-up — the questions guests ask after receiving your pre-arrival sequence. If a guest replies to your 24-hour message asking about early check-in availability, or sends a check-in-day question in Spanish, Guestar responds instantly from your property knowledge base without you needing to be available. It works alongside your Hostaway triggered messages rather than replacing them: your sequence handles the broadcast, Guestar handles the conversation.

What's the best timing for a pre-arrival message sequence in Hostaway?

At booking (immediately), 24 hours before check-in, and 2 hours before check-in. The 24-hour message is the most important because guests are actively preparing for travel — they'll read and act on logistics at that point. Earlier than 24 hours and guests often forget the details; later and they may already be en route without time to process them.