Guest messaging goes wrong in two directions. Too little, and the guest arrives uninformed and resentful. Too much, and you become the host who sends eleven notifications for a weekend away.
Five messages covers a short stay properly. Each one exists because there is something the guest needs at that moment and cannot use earlier.
1. A week before: the practical questions
Sent seven days out, when plans are still flexible enough to change.
Hi Sara — you're with us a week today. Two quick things so I can get everything ready:
Are you driving? If so I'll send parking details, they're a bit particular.
Roughly what time do you think you'll arrive? No commitment, just helpful for me.
The guidebook for the flat is here if you want a look at the area before you come: [link]
Anything you need, just ask.
Two questions and a link. The parking question is the important one — it lets you send 200 words of parking detail to the people who need it and none to the people who don't. The arrival time question catches early arrivals while there is still time to plan for them.
2. The night before: everything needed to get in
The most important message of the five, and the one most hosts send on the morning of arrival instead.
People read travel messages the night before they travel. On the day itself they are in transit, on a bad connection, with a low battery.
Evening Sara — all set for tomorrow.
Address: 14 Marden Street, Brighton BN2 1TR. In a taxi, "Marden Street by the Co-op" works better than the postcode.
Getting in: door code 4729, then press the tick key below the 9. Green door with a brass letterbox, set back behind the hedge. Lockbox on the right of the porch, under the mailbox.
Time: any time after 4pm, nobody to meet. If you're early, there's a covered side passage to the left of the porch where you can leave bags.
WiFi: network
MardenHouse, passwordseagull-harbour-92— putting it here in case you've no data when you arrive.Everything else is in the guidebook: [link]. I'm about all evening tomorrow if anything's odd.
Plain text for the code and the password. A guest with no signal standing in a hallway needs those readable in the message itself.
3. Check-in morning: the light touch
Short. Its job is to be the most recent message in the thread when the guest lands, so the details are one scroll away rather than twenty.
Morning — the flat's ready and the code's live from noon. Safe travels, see the note below for everything you need.
That is it. Three lines. If you have nothing to add, add nothing.
4. Midway: the one that saves reviews
Sent on the morning of day two, not day three. The timing is the whole point — early enough that a problem can still be fixed within the stay.
Morning Sara — hope the first night was good. Anything not right with the flat, tell me and I'll sort it today. Also happy to answer anything about the area; the rainy-day bit of the guidebook is genuinely useful if the forecast holds.
Two things happen. Some guests report a small problem, which you fix, which converts a four into a five. Most reply "all great, thanks", which is also useful — it is a written record that the guest was happy on day two, and it makes a surprise complaint afterwards much easier to handle.
Do not send this on the last day. A problem reported on the last day is a problem you cannot fix.
5. The evening before departure: tomorrow's plan
Hope the week's been good. Check-out is 10am tomorrow — nothing to clean, genuinely. If you could put food waste in the green bin by the side gate, shut the windows including the small bathroom one, and leave the keys in the lockbox, that's everything. Pull the front door firmly until it clicks.
If you need an extra hour, say the word, I can usually manage it.
Thanks for being easy guests, and safe trip home.
Evening, not morning, for the same reason as the arrival message: this is when people plan tomorrow. It also gives you one last chance to hear about a problem.
What not to send
A sixth message asking for a review. The platform already does this. A host asking on top reads as pressure, and it tends to arrive at exactly the moment a guest is dealing with a delayed train.
Anything promotional. Discount codes for a return stay, requests to follow you somewhere. The stay has not finished being earned yet.
A message with no purpose. If you find yourself writing "just checking in!" with nothing after it, delete it. Every message spends a small amount of the guest's patience, and you want that budget available for the ones that matter.
Automate the schedule, write the words yourself
The five slots are the same for every guest. The contents are the same for every guest apart from a name and a date. That is exactly the shape of thing worth scheduling once and forgetting.
What should not be automated is the tone. The templates above took me a long time to get right, and they read as though a person wrote them because a person did. A scheduled message that sounds like a system produces a guest who stops reading your messages by day two, which defeats the entire point of sending them.