Hey
Great question. Automatic messages have honestly been a game changer for us.
If you are looking to scale or just protect your sanity on busy weeks, they are invaluable. They make sure your guests always get clear, consistent communication even when you are slammed, travelling, or simply do not have the energy to
rewrite the same message again.
Here is how we approach it.
1- Thank you for booking sent immediately after confirmation
This is more than just a confirmation.
It is your first brand touchpoint.
We use it to welcome them warmly, get them excited about the stay, and set expectations around house rules early.
I like including key house rules here such as quiet hours, pets, and smoking. If anything does not suit them, better to surface that early rather than risk a poor stay or review. It saves everyone time.
2- Check in message sent one to two days before arrival
This needs to be crystal clear. No ambiguity.
We include the exact address, step by step directions, clear instructions for lockboxes with photos, parking information, how to access the building, and links to our digital guidebook.
The more visual and simple you make this, the fewer how do I get in messages you will receive late at night.
3- Hope you are settling in message sent around three hours after check in. This one is really important.
We send a short note saying we hope they are settling in well and to let us know immediately if anything is not right. Problems cannot be fixed after checkout, so we encourage guests to raise things early.
It makes them feel supported even though it is automated, and it dramatically reduces negative surprises later.
4- Last night or pre checkout message. We thank them for staying and gently remind them about checkout time and what needs to be done such as bins, dishes, and keys.
Clear expectations create smoother turnovers.
5- Post checkout thank you
A few hours after checkout, we send a genuine thank you, remind them that we have other properties in the area, and let them know they are welcome back anytime. Sometimes we also mention a returning guest incentive.
Repeat bookings are gold, and this message quietly supports that.
We also use Quick Replies for one off topics such as how to operate heating, fishing permits, local nightlife recommendations, or appliance instructions. It means we are not rewriting the same answers constantly.
For us, automation is not about being robotic. It is about creating reliable touchpoints so guests always feel guided and supported, while freeing us up to focus on what actually grows the business, maintaining the listing, optimizing pricing, and refining the experience.
When done right, automated messages feel warm, not automated.
Hope that helps.
DM me if you want some templates
