Phones & Front Desk

The Three Questions Every Guest Texts Before They Check In

RI AI Agency · 2026-10-19 · 5 min read

It's a little after eleven on a Saturday, checkout's done, and you've got three rooms to flip before the next guests arrive. Your arms are full of sheets. Your phone's buzzing on the dresser, and you already know roughly what it says.

"Hi! What time can we check in?" "Is there parking?" "How far to the beach?" Maybe a fourth: "Can we bring the dog?" Same handful of questions, every week, from nearly every guest.

None of them is hard. That's the frustrating part. You know the answers cold, you've typed them a hundred times, and they always land right when you're mid-turnover with a mattress half-made and twenty minutes of daylight to spare.

The questions you already know by heart

Before you automate anything, write down what guests actually ask. For most Newport inns, B&Bs, and short-stay hosts, the pre-arrival texts cluster into four:

If you handle more than one property, do this per property. The parking answer for a place off Thames is not the parking answer for a place up by the hospital.

Set up the auto-reply first

An auto-reply is a message that goes out on its own the moment a guest texts or messages you, so they get an answer in seconds even if you're elbow-deep in a turnover. If you book through Airbnb or Vrbo, scheduled and instant messages are built in. If guests text your business line, most texting tools (and Google Voice) can fire an automatic first reply.

Keep it short and front-load the four answers. Something like this works:

That one message kills most of the back-and-forth. The guest feels looked after, and you didn't touch your phone.

Then the morning-of arrival text

The auto-reply handles the curious guest who messages days ahead. The morning-of text handles everyone else, the ones who never ask and then call you at 2:45 from your own driveway.

Schedule one text to go out the morning each guest arrives. This is the one that carries the day's real specifics:

You can set these to send at, say, 8 AM so guests read them over breakfast, long before they're loading the car. A booking platform can schedule these off the reservation date. A simple texting tool can too. Either way you set it once and it runs.

What you should still answer yourself

Automation is for the predictable stuff. The judgment calls stay with you, and trying to canned-answer them will cost you more than it saves.

Here's the honest limit: automation is great at the questions that have one right answer and terrible at the ones that need a read on the situation. If a text makes you pause even a second to think, that's a you text, not a robot text. The trick is letting the canned answers clear the easy 80 percent so you've got the time and patience for the 20 that matter.

Keep the answers current as the season turns

A stale auto-reply is worse than none. If your text says "park on the street" and the city's posted a residential permit block since you wrote it, you've just sent a guest toward a ticket with your name on the recommendation.

Newport doesn't sit still. Parking rules shift, beach lots fill differently in season, meters run some months and not others, and your own hours loosen up once sailing season gets going. Put a standing reminder on your calendar to reread every canned message when things change:

Reading them out loud takes five minutes. Do it as the guest, not the owner, and you'll catch the line that made sense in April and misleads in July.

Worth doing this week

You don't need a system. You need two good messages and a habit of keeping them honest. Start here:

  1. Scroll your last month of guest messages and jot the four questions you answer most. For most hosts it's parking, check-in, beach, and the dog.
  2. Write the auto-reply. Four short lines, the answers front and center, a warm sign-off. Turn it on in your booking platform or texting tool.
  3. Draft the morning-of arrival text with the door code, the exact parking spot, and your cell. Schedule it for around 8 AM on arrival day.
  4. Decide out loud what stays human: early check-in, special requests, anything that sounds like trouble. Don't automate those.
  5. Put a reminder on the calendar to reread both messages when the season flips or a parking rule changes.

If you'd rather hand this off, wiring up auto-replies and scheduled arrival texts is the kind of small, quick job we do for Newport hosts all the time. Either way, the goal's the same: the easy questions answer themselves, and you get your turnover back.

Want this working in your business?

We build and manage systems like this for Rhode Island small businesses, scoped in plain English and priced flat.

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