How to Write a Message to a Repeat Guest Who May Rebook

A good message to a repeat guest reads like a note from someone who remembers them, not a marketing blast. Mention something specific from their last stay, then let them know the property has openings, without pushing for a booking in the same breath.

Why message returning guests directly

A guest who already stayed with you skips most of the questions a new guest asks. They know the house, the parking, and roughly what to expect. That familiarity is worth something, and a direct message is how you cash it in before a busy season fills up.

Booking platforms rarely resurface past guests to you on their own. If you want a guest from two summers ago to think of your property again, someone has to remind them it exists. A short, personal message does that far better than hoping they scroll back through their trip history.

This only works if the past stay went well. A guest who left frustrated wants to be left alone. Reserve this outreach for stays that ended on good terms.

How you send the message depends on where the original booking came from. A direct booking usually leaves you with the guest's email address. A platform booking may limit you to the platform's message thread, since platforms often mask contact details. Check the platform's rules before you take that conversation anywhere else.

Timing your outreach message

Reach out a few months before the season they stayed in last time. A guest who visited in July of last year is a natural fit for a message in early spring, before their summer plans are set.

Also watch your own calendar for open weeks. A message that names a specific opening gives the guest something concrete to act on. A vague "come back sometime" note with nothing to book against gives them nothing to answer.

Avoid sending this message during your busiest weeks, when you have nothing open anyway. There is little point inviting someone back to dates that do not exist.

A short list of past guests sorted by their original travel month makes this timing easy. Send outreach in small batches, a few messages a week, rather than one mass message to everyone on the same day.

Sample message to a repeat guest

Hi [name], hope you have been well since your stay with us last August. I still think about how much your kids loved the dock. We have a few weeks open this coming July if you are thinking about another trip up. No pressure at all, just wanted you to have first chance before those dates go.

Notice what that message does. It opens with something specific to their trip, mentions availability once, and then stops selling. More outreach wording, including the follow up for a guest who does not reply, lives in the guest messaging master pack.

Mentioning availability without pressure

State the open dates plainly and move on. A message that circles back to the booking three times in five sentences turns into a pitch, and pitches make people defensive.

One clean sentence with the dates does the job. A line naming the second week of July as open tells the guest exactly what to check against their own calendar, without any extra selling around it.

Skip any language about deadlines or limited spots. A returning guest already likes the property. A reminder and an easy way to say yes is all it takes.

End the message with an easy out. "No pressure at all" or "just wanted you to know" gives the guest room to say no without feeling like they owe you an explanation.

Should you offer a returning guest discount?

A discount is optional, and the invitation itself does most of the work. A guest who loved the place is deciding between coming back and trying somewhere new. The reminder usually settles that on its own.

If you do offer one, keep it small and tie it to the booking you want. Returning guest discounts commonly sit between 5% and 10% off the nightly rate. On a direct booking you simply quote the lower rate. On a platform booking, use the platform's own tools, such as the special offer with a custom price that Airbnb lets hosts send, as of this writing. A discount promised in a message but never applied at checkout causes exactly the kind of dispute this outreach is meant to avoid.

Point any discount at the dates you need filled, never at peak weeks that book themselves. A value add can work better than a rate cut. Early check in, late checkout, or a stocked firewood rack often costs less than 5% off a week and feels more personal to the guest.

Subject lines for emailing direct guests

A past direct guest gave you an email address, and the subject line decides whether the message gets opened. Phone mail apps commonly cut subjects off around 30 to 40 characters, so put the property and the season in the first few words. Skip sale wording like "limited" or "last chance", which pushes a personal note toward the promotions folder.

• July weeks at the lake house are open
• Your August week is open again this year
• Early look at summer dates at the cabin

Each of those works because it says something true and specific. The guest can tell from the lock screen who it is from and why it matters to them.

Personalizing the message with past details

Pull one real detail from the last stay: a request they made, something they mentioned loving, or a small thing you fixed because of their feedback. That detail is what makes the message land as personal instead of automated.

If the guest already left a review, that review is often the easiest source of a detail to reference. The habit starts with the post stay thank you message, and asking guests for reviews the right way covers the step right after it. A guest you already know this well also skips most of the screening questions a stranger would get.

Keep notes on past guests somewhere you can find them later, even a simple spreadsheet with a line per stay. Six months after checkout, most hosts cannot recall which guest asked about the kayak or which family had the toddler who loved the fire pit. A single line is enough: the dates they stayed, one detail worth remembering, and anything they asked you to fix. That line takes thirty seconds to write right after checkout. A year later it hands you the opening sentence of this exact message.