The Complete Timeline for Guest Communication (What to Send and When)

Guest communication isn't complicated. But getting the timing wrong makes even good messages feel like spam or, worse, silence when a guest needed to hear from you.

The hosts with the best reviews tend to follow the same pattern: the right message, at the right time, with the right amount of information. Not too much (guests stop reading), not too little (guests start worrying), and never too late (guests lose trust).

Here's the complete timeline. Seven touchpoints from the moment a guest books to a week after they leave. Each one has a purpose, a timing window, and a guide to what should be in it.

The Timeline at a Glance

That's seven messages across a typical stay. Some stays need all seven. A one-night stay might need four. Adapt the timeline to the length of the stay, not the other way around.

Message 1: Booking Confirmation (Within 1 Hour)

When: As soon as possible after the booking is confirmed. Ideally within an hour. If you use Instant Book (and you should), this message can be automated.

Purpose: Reassure the guest that they've booked a real property run by a real person. The moment between clicking "Book" and hearing from the host is when buyer's remorse is strongest. A fast, warm response kills that anxiety.

What to include:

• Thank them for booking

• Introduce yourself briefly (first name, one sentence about you)

• Confirm the dates and number of guests

• Let them know you'll send check-in details closer to their arrival

• Invite them to ask questions

What NOT to include:

• Check-in instructions (too early, they'll forget)

• A wall of house rules (sets a negative tone)

• Your entire guidebook (overwhelming)

Example:

Hi [name], thanks for booking! I'm Bart, your host. Just confirming your stay from [date] to [date] for [number] guests. I'll send over check-in details a day or two before your arrival. In the meantime, let me know if you have any questions at all. Looking forward to hosting you!

Keep it under 100 words. The guest doesn't need a novel. They need to know a human is on the other end.

Message 2: Pre-Arrival Message (1-2 Weeks Before)

When: Seven to fourteen days before check-in. For bookings made less than a week out, send this immediately after the confirmation message.

Purpose: Share your digital guidebook, collect logistics, and give the guest everything they need to start planning the practical side of their trip.

What to include:

• A link to your guidebook (with house rules, local recommendations, and property info)

• Ask for their estimated arrival time

• Parking details if relevant

• Any seasonal notes (e.g. "the outdoor shower is turned off in winter" or "the pool is heated from May to September")

What NOT to include:

• Full check-in instructions (save those for the day before)

• A detailed house manual (that's what the guidebook link is for)

Example:

Hi [name], your stay is coming up! Here's a link to our guest guidebook: [link]. It has everything you need, including house rules, WiFi details, and our favourite local restaurants.

A couple of quick questions: roughly what time are you planning to arrive? And will you be driving (so I can share parking info)?

Talk soon!

This message does two things at once. It delivers information and it collects information. The arrival time lets you prepare the property (or brief your cleaner). The driving question lets you tailor your directions.

Message 3: Check-In Instructions (Day Before Arrival)

When: The day before check-in, ideally between 2pm and 6pm. Late enough that the guest is in "trip mode" and thinking about logistics. Early enough that they can read it and plan their morning.

Purpose: Give the guest everything they need to get from wherever they are to inside your property without calling you.

There's a full guide on how to write self check-in instructions your guests will actually follow, but the essentials are:

What to include:

• Address (with a note if Google Maps sends people to the wrong spot)

• Step-by-step entry instructions (lockbox code, smart lock pin, key location)

• Photos of the entrance if it's not immediately obvious

• WiFi network name and password

• Your phone number for emergencies

• Check-in time reminder

What NOT to include:

• Checkout instructions (wrong time, they'll ignore them)

• Local recommendations (those live in the guidebook)

• Anything that requires more than two minutes to read

The golden rule of check-in instructions: a tired guest arriving after dark with a suitcase and a phone should be able to follow your instructions and get inside without hesitation. If your instructions require more than five steps, simplify the process before you simplify the message.

Message 4: First-Night Check-In (Evening of Arrival Day)

When: Two to four hours after the guest's estimated arrival. If they arrive at 4pm, message around 7pm. If they arrive at 9pm, message the next morning instead.

Purpose: Confirm everything is working and catch problems while they're small. A guest who discovers a broken shower on night one and doesn't hear from you will stew on it for the entire stay. A guest who mentions it and gets an immediate "I'll send someone in the morning" feels looked after.

What to include:

• A short check that they got in okay

• Ask if everything is working and if they need anything

• Nothing else

Example:

Hi [name], just checking you got in okay and everything looks good! Let me know if you need anything at all. Enjoy your evening!

Two sentences. Maybe three. This message is not an opportunity to remind them about house rules or sell them on your guidebook. They're settling in. Respect their time.

When to skip this message: if the guest has already messaged you confirming they've arrived and everything is fine, don't send it. They've already told you what this message was going to ask.

Message 5: Mid-Stay Check-In (Optional)

When: Day two or three of a stay that's four nights or longer. Skip this entirely for one or two night stays.

Purpose: Light-touch presence. You're not checking up on them. You're making yourself available without being intrusive.

What to include:

• A casual "hope you're having a great time"

• One specific recommendation based on the weather, the day, or the season (e.g. "If you're looking for dinner tonight, [restaurant] does a great [dish] on Thursdays")

• A reminder that they can reach you if needed

Example:

Hi [name], hope you're enjoying the stay! If you're looking for something to do today, [specific recommendation]. Let me know if you need anything.

When to skip this message: short stays (one to three nights), guests who've been communicating already, or guests who clearly want minimal contact. Read the room. Some guests love hearing from the host. Others booked a vacation rental specifically to avoid human interaction.

This is also a good moment to share a specific guidebook section if relevant. "By the way, there's a list of our favourite walks in the guidebook if you fancy getting out tomorrow" feels helpful, not salesy.

Message 6: Checkout Instructions (Evening Before Departure)

When: The evening before checkout, between 6pm and 8pm. This gives the guest time to read it, pack without feeling rushed, and plan their morning.

Purpose: Tell the guest what to do before they leave so your property is ready for the next guest (or your cleaner).

There's a full guide with copy-paste templates for checkout instructions, but the key principles:

What to include:

• Checkout time

• Where to leave the keys

• What to do with rubbish

• Any specific asks (start the dishwasher, put towels in the bath, lock windows)

• A thank you

Keep it to five or six items maximum. Every item beyond that reduces the chance any of them get done. Your cleaner handles the deep work. You're just asking guests to do the basics.

What NOT to include:

• Threats about additional cleaning fees

• A request to strip beds, mop floors, or deep clean (that's what your cleaning fee covers)

• Your checkout instructions inside a larger message about something else (send checkout as a standalone message so it's easy to find on departure morning)

The tone matters. A checkout message is the last thing a guest reads from you before they write a review. "Thanks for being a great guest, here are a few quick things before you head off" lands very differently from "Please ensure all items on the following list are completed prior to departure."

Message 7: Thank You + Review Request (1-2 Days After Checkout)

When: 24 to 48 hours after checkout. Same day is too soon (they're travelling). Three or more days later and the stay has faded from memory.

Purpose: Close the relationship on a warm note and prompt a review. This message directly affects your review rate, which directly affects your search ranking and your path to Superhost.

What to include:

• A genuine thank you (mention something specific about their stay if you can)

• Ask if they'd be willing to leave a review

• Your direct booking website link for future stays

Example:

Hi [name], thanks again for staying with us! Hope you had a great time and the journey home was smooth.

If you have a minute, I'd really appreciate a review. It makes a big difference for small hosts like me.

And if you're ever planning another trip to [area], you can book directly through our website next time for a better rate: [link]. Same property, same host, no Airbnb fees.

Safe travels!

That last paragraph is doing important work. The guest has completed their stay. They're off-platform. This is the right moment to mention your direct booking website. You're not violating Airbnb's terms. You're offering a returning guest a better deal on a future visit.

For the full strategy on converting one-time guests into returning bookers, there's a dedicated guide on turning guests into repeat direct bookers.

How to Get a Five-Star Review from Your Communication Alone

Guest communication is one of the six categories Airbnb asks guests to rate. A perfect score here is entirely within your control because it depends on exactly two things: speed and helpfulness.

Speed. Respond to every message within an hour during waking hours. If you can't, set up auto-replies that acknowledge the message and give a realistic response time. Airbnb tracks your response rate and response time, and both feed into your search ranking.

Helpfulness. Answer the question they asked, plus the question they're about to ask. If a guest asks "what time is check-in?" reply with the check-in time AND the check-in process, because that's the next thing they'll want to know. Anticipating the follow-up question saves both of you a round trip.

Saved replies. Set up templates in Airbnb's messaging for the questions you get every week: directions, parking, restaurant recommendations, checkout process, WiFi. A fast, thorough reply from a template is better than a slow, custom reply every time.

Automation vs Personal Touch

You can automate messages 1, 3, and 6 (booking confirmation, check-in instructions, checkout instructions) because they're the same for every guest with minor variable swaps (name, dates, arrival time). Airbnb's scheduled messages feature handles this natively, or tools like Hospitable and Guesty automate it with more flexibility.

Messages 2, 4, 5, and 7 (pre-arrival, first-night check-in, mid-stay, post-stay) benefit from a personal touch. A guest can tell the difference between "Hope you're having a great time!" sent by a bot and "Hope you're enjoying the sunshine today, perfect weather for the coastal walk I mentioned in the guidebook." The personal version takes 30 seconds more and is worth significantly more in review sentiment.

The ideal setup: automate the operational messages so they never get missed. Write the personal messages yourself so they never feel generic.

Putting It All Together

Print the timeline table from the top of this article and pin it near your desk. For each stay, work through it in order. After a dozen guests, the pattern becomes second nature and the messages start writing themselves.

The hosts who communicate well don't send more messages. They send better-timed ones. A guest who gets the right information at the right moment feels looked after without feeling managed. That feeling shows up in reviews. Those reviews show up in your ranking. And that ranking brings you the next guest.

If you want all of this in one place that the guest can access on their phone, a digital guidebook replaces half of these messages with a single link. Build a guidebook with your house manual, house rules, check-in details, and local tips. Send the link in your pre-arrival message. The guest has everything before they arrive, and the only messages left to send are the personal ones.