Build a list of past guests who have agreed to hear from you, then send each a short sequence timed to their stay: thank-you, a memory with a local tip, an early-rebooking offer, then seasonal short-break and gap-filling emails. AI drafts the wording from your booking data; you supply the facts and offers a marketplace cannot match.
The first catch is the list itself. Airbnb's terms of service (I read the edition last updated 5 February 2026; some regions have their own editions, so read yours) say you may only use another member's personal information as necessary to facilitate a transaction. They bar commercial messages to members without their express consent, and bar taking bookings or payments outside the platform. So guests who found you through a marketplace are not automatically yours to email. Your list should come from people who booked or enquired with you directly, plus anyone who has asked to hear from you.
Who belongs on a past-guest list, and who does not
Most holiday cottage marketing advice starts with adverts and directory listings. This starts with people who have already stayed, because they know the place, they cost almost nothing to reach, and a direct rebooking avoids a marketplace's commission.
Sort every past guest and enquirer into one of three groups before you export anything.
- Booked direct by phone, email or your own website. These are the core of the list. Ask permission at booking and again at check-out, and keep the date and the way they agreed.
- Enquired but never booked. They asked a question, which is not the same as asking for marketing. Leave them off unless they said they wanted updates.
- Booked through a marketplace. Keep them in the marketplace's messaging. Airbnb's terms also bar encouraging guests to open accounts or otherwise interact with a third-party site before, during or after a reservation, so a sign-up card in a marketplace guest's welcome pack is a risk. Whether you may take a later booking directly from someone you first met on a marketplace depends on that platform's terms. Read them, and when in doubt, ask the platform's support team.
If you host both kinds of guest, give the sign-up card only to direct guests, for example in a direct-booking welcome email rather than a card in every cottage. A short permission line works well on the booking form and on that card: "Would you like first pick of dates and the odd short-break offer? We email about six times a year and you can leave at any time." Marketing-email rules differ from country to country; in many places you need clear consent or a documented lawful basis, plus a working unsubscribe link in every message. Ask your data-protection adviser or your email tool's compliance pages what applies to you.
The sheet behind the list needs fewer columns than you might expect, and none of them should be an email address when you work with AI.
| Column | Example | What it is for |
|---|---|---|
| guest_id | G0412 | Lets you show AI a row without a name or address |
| first_name | [first name] | The greeting |
| cottage | Cottage A (sleeps 4) | Which stay to mention |
| arrival, nights | 5 Sept, 7 | Timing of the rebooking email and the season of their stay |
| adults, children, dog | 2, 0, yes | Segments such as dog owners or family weeks |
| how_booked | direct | Whether they are eligible at all |
| consent_date, consent_source | 2 Sept, booking form | Your proof of permission |
| note | Walked the coast path daily | One true detail for the memory email |
Write notes you would be comfortable showing the guest. Keep email addresses in your email tool and the booking system only; when you paste rows into an AI chat, paste the guest ID and first name. The wider question of what is safe to share is covered in this tutorial on putting customer data into ChatGPT.
One guest's year: six emails and when to send each
Think of two tracks. The first is personal and triggered by a stay, so each guest has their own clock. The second is a seasonal broadcast to chosen segments. This is the first track plus the two broadcasts that most cottages need.
| When | Its one job | Example subject line | |
|---|---|---|---|
| 1. Thank-you | 2 days after departure | Thank them and ask one private question about the stay. Nothing to buy. | Thank you for staying, [first name] |
| 2. Memory and a tip | About 3 weeks later | One thing they enjoyed, from your note, and one thing they missed, from your list of places nearby | The walk we should have mentioned |
| 3. First pick | About 5 months later | Hold the same week next year for them before it opens to everyone | Your week next year, before it goes public |
| 4. Seasonal short break | Twice a year, to chosen segments | A dated offer on quiet midweek stays | Four midweek nights in [month], one rate |
| 5. Gap-fill | 3 to 4 weeks before dates that are still empty | A small, dated offer on open nights | Open nights at [cottage name] on [date] |
| 6. Anniversary | 12 months after the stay | "A year ago you stayed": first pick of next year if they have not booked | A year since [cottage name] |
Two rules keep this from becoming a nuisance. Suppress anyone who already has a future booking in your diary, or they will receive an offer for a stay they have already made. And send emails 4 and 5 only to segments they suit: a family-week offer to a couple who came in November is noise.
The running example is an owner of two self-catering cottages, one sleeping four at about $120 a night and one sleeping six at about $165. Five years of records show 410 stays, 140 of them booked direct and 270 through marketplaces. After removing duplicates there are 96 direct guests with a recorded permission, 28 of whom have stayed more than once. That list of 96 is the audience; the other 270 stays are not, however good the addresses look in the export. The rest of this tutorial uses that owner and those numbers, which are illustrative.
The thank-you and the first-pick emails, written out
Email 1 is short because its job is goodwill. Email 3 is the one that earns bookings, so it deserves the most care. Both use placeholders in square brackets, which are the facts you fill in from the sheet.
Subject: Thank you for staying, [first name]
Hello [first name],
Thank you for choosing [cottage name] this week. I hope [one detail from the note] was as good as it sounds in the visitors' book.
If anything was not right, just reply to this email. I read every reply myself.
[your name]Subject: Your week next year, before it goes public
Hello [first name],
Bookings for [month, year] open to everyone on [date]. Because you stayed with us, I am holding [arrival date] to [departure date] for you until [date, ten days earlier].
The direct rate is $[amount] for the week, and I will include a welcome hamper if you book by [date]. Reply to this email, or use [link], and I will confirm the same day.
If that week does not suit, tell me which one does and I will say what is free.
[your name]Two practical points about email 3. Holding a week is a real cost, because for ten days it cannot be sold to anyone else, so offer it only for weeks that are not already selling quickly, and put the release date in your own diary. Second, if you also list on a marketplace, check its agreement for any rate-parity clause (a promise not to advertise a lower price elsewhere) before publishing a direct rate that is lower than the marketplace rate. A private offer to your own past guests is different from a public price, but ask the platform whether it counts; do not assume.
Offers that keep your rate and still fill the diary
A blanket discount teaches guests to wait for the code. The better offers cost little, are dated, and apply only to nights that would otherwise stay empty. Here are five, with their cost to you worked out on the two cottages.
| Offer | What it costs you | Best used for | Guard rail |
|---|---|---|---|
| First pick of dates | $0, but the week is held for ten days | Next year's peak weeks | Hold only weeks that are not selling fast |
| Welcome hamper | About $18 of goods (illustrative) | Rewarding a direct booking without touching the rate | Make it for bookings made by a date |
| Late checkout | $0 if the next arrival is a day away; otherwise a cleaner's overtime | Sunday or midweek departures | Check the next arrival before you promise it |
| Midweek short break, 15% off | $72 off a $480 stay of four nights at $120 | Quiet months, Monday to Friday | Only on dates that show as free today |
| Gap-fill, 20% off | $48 off a $240 stay of two nights at $120 | Two or three orphan nights between changeovers | Send once, with an end date |
Read the two percentage offers the right way round. The midweek stay gives up $72, but if those four nights would have stayed empty you are $408 better off, not $72 worse. If they would have sold anyway at full price, you have just given a guest a discount for nothing. That is why the guard rail on every row is the same: look at the diary on the day you send. If your booking system can export unsold nights by month, the routine in this tutorial on occupancy and rate reports will find your quiet dates in minutes.
Prompts that draft the sequence in your own voice
Do this once, then reuse it. Collect three emails you have written to guests that sound like you, and ask an AI assistant to describe your style as a short list of rules. Save the rules in a ChatGPT Project, a Claude Project or a Gemini Gem (becoming a skill from November 2026), so every later draft starts from them without pasting them in again.
Read these three emails I sent to holiday guests. Describe how I write as eight short rules (sentence length, greeting, sign-off, words I use, words I avoid, how I handle a problem, how I ask for something). Do not flatter me. Quote a phrase from the emails as evidence for each rule.
[paste three emails with names removed]Then draft email 3 from the facts only. Here is the prompt and what a first run tends to return.
Using my style rules above, write email 3 for past guests who booked direct. Use only these facts: first name [first name]; they stayed in [cottage name] from [arrival] to [departure]; the same week next year opens to everyone on [date]; I am holding it for them until [date]; the direct rate is $[amount]; a welcome hamper is included if they book by [date]; they can reply or use [link]. Under 150 words, one call to action. Give five subject lines under 45 characters. Do not invent any detail about their stay or the area.A first run might return (illustrative) five subject lines, one of them "Last chance to book your week!", and a 140-word email that says "we hope the log burner kept you warm". Two fixes. The "last chance" line is untrue because nothing ends on that date for the public, so delete it. And the log burner was invented: the facts never mentioned one and Cottage A does not have one. A personalised email with a wrong detail is worse than a plain one, which is why the prompt says to use only the facts given and why you read every draft aloud before it goes out.
The same approach handles the list. Paste the sheet without addresses and ask for segments with counts.
Here are rows from my past-guest sheet (guest_id, cottage, arrival, nights, adults, children, dog, how_booked, consent_date). Group the guests into: stayed in the last 12 months; 12 to 24 months ago; stayed more than once; travelled with a dog; midweek stays. A guest can be in several groups. Give a count for each group and list the guest_ids. List every row with no consent_date separately.For the 96 guests the result might read: 31, 22, 28, 40 and 17. It might also list two rows with no consent_date, although every guest on the list gave permission: in this illustration the date had been typed into the note column at check-out. Move it to the right column before those two are emailed, and leave off anyone whose permission you cannot find a record of. Always recount one segment yourself with a filter in your spreadsheet, because assistants miscount long lists, and a wrong count means the wrong people get the wrong offer.
A fourth, quieter use: paste in the comments from your visitors' book or feedback emails (names removed, and only comments guests wrote for you) and ask what guests mention most. If the answer is the dog-friendly garden and the quiet, your short-break emails should talk about those, not the kitchen you were proud of. To check the finished drafts before they go out, this email QA checklist is worth running down once.
Local-area content that does not go stale
Email 2 and the seasonal broadcasts work best when they carry something useful about the area around the cottage, not a sales pitch. The risk is accuracy: an assistant will happily recommend a tearoom that closed last year. So the rule is that AI writes only about places on your own list, and you keep the list.
Place: [name]
Type: walk / pub / café / farm shop / attraction
Distance from the cottage: [minutes on foot or by car]
Best in: [season]; wet-weather option: [yes/no]
Dog-friendly: [yes/no], checked on [date]
Opening days: [verify before every send]
Why guests like it, in my words: [one sentence]Filled in, one entry might read like this (illustrative):
Place: the reservoir loop
Type: walk
Distance from the cottage: 10 minutes by car, then 4.5 km on a level path
Best in: spring and autumn; wet-weather option: no
Dog-friendly: yes, on leads near livestock, checked on 2 March
Opening days: car park all year; the café at the dam opens Wed to Sun [verify before every send]
Why guests like it, in my words: flat enough for a pushchair, and you see the whole valley without a climb.Keep about twenty entries, and when you use one, check it on the day. Then ask for the note itself.
Using ONLY the places in the list below, write a 120-word note for my March short-break email: one walk, one place for lunch, one wet-weather option. For any place whose "Opening days" says verify, add "[check before sending]" after its name. Do not add any place that is not in my list.The difference shows most in a seasonal broadcast. Here is a typical first attempt, then the version built from the diary and the list (both illustrative).
Before: Autumn is a magical time to escape to the countryside! Enjoy 10% off all autumn stays at our cosy cottages. Book now!
After: Four midweek nights in Cottage A, Monday 9 to Friday 13 November, $408 instead of $480, for guests who have stayed with us before. The reservoir loop is at its best in late autumn: level, about 4.5 km, dogs welcome on leads, and the café at the dam is open Wednesday to Sunday [check before sending]. Reply to hold the dates; the offer closes on 23 October.The second version names the dates, the price, one reason to come and an end date, and it discounts only four nights the diary shows as empty. The first gives 10% away on every autumn stay, including the ones that would have sold at full price, and tells a past guest nothing they did not already know about the place.
A rough calendar gives the broadcasts a theme without inventing events: a winter walking break in January, a first-lambs or spring-blossom weekend in March and April, a bank-holiday gap-filler in late spring, a half-term family week, an early-September "quiet weeks" note, and an autumn dog-friendly walking list. Use event dates only if you have confirmed them from the organiser. For longer guest-facing material built from your own notes, the approach in this guide to B&B descriptions and guest guides carries over to cottage welcome books.
What the sequence costs and what one rebooking pays back
Back to the owner with the list of 96. Setting up (voice rules, six emails, two offers, sign-up wording) takes about four hours with an AI assistant, in my estimate. Each later send takes around 25 minutes to adapt, check and schedule; with seven sends in a year that is just under three hours. At a notional $25 an hour, the year's effort is about $175 of time.
The tool itself may cost nothing at this size. Mailchimp's free plan has been listed at 250 contacts and 500 sends a month, and MailerLite's pricing page shows a free plan for up to 250 subscribers and 2,500 emails a month, with automations included. Brevo's free plan sends up to 300 emails a day once your account is approved. Paid plans start around $9 a month for Brevo's Starter on monthly billing and $12 a month for MailerLite's Comfort at 500 subscribers, and the price climbs with list size, so confirm both on the live pages. A list that has grown to 400 would add roughly $100 to $160 a year.
Now the pay-back. One four-night midweek stay at $120 a night, sold at 15% off, brings in $408. If those nights would have stayed empty, that single booking more than covers the year's time on the small list. Commission is a bonus and not the reason: if the same $480 booking would otherwise have come through a marketplace that takes, say, 15% in commission and payment charges (check your own agreement), you keep $72 more. That alone will not pay for four hours of work. The case rests on filled dates and on guests who return, and on those the arithmetic is comfortable: one extra booking a year pays for the effort, and anything beyond it is profit.
Sending rules: permission, frequency and complaints
Send from a real person's name and address, with a plain-looking layout, a clear sender line and an unsubscribe link in every email. Keep to the six or seven sends in the table, never two in a week, and send the personal ones (1 to 3 and 6) when their clock says so rather than in batches.
Google's email sender guidelines ask every sender to keep the spam rate shown in its Postmaster Tools below 0.10% and never to let it reach 0.30%; extra rules, such as one-click unsubscribe, apply to senders of more than 5,000 messages a day. The arithmetic is what matters at your size: on a list of 96, a single complaint is already about 1%. That is a good argument for a list made only of people who asked, and for making unsubscribing a one-click job, which also protects your sending address's reputation with mailbox providers.
Do not make decisions from open rates. Judge each send by replies, link clicks and bookings. A reply is worth far more than an open, so end every email by asking for one thing only.
How to measure it with one spreadsheet
Give every email its own link tag (for example ending ?src=e3) or its own code word for phone and email bookings, and record every booking against a source in your diary. A year later one sheet answers the question.
| Sent | Clicks | Enquiries | Bookings | Revenue | |
|---|---|---|---|---|---|
| 3. First pick | 96 | 21 | 9 | 5 | $3,150 |
| 4. Seasonal short break | 96 | 15 | 4 | 2 | $816 |
| 6. Anniversary | 28 | 6 | 2 | 1 | $600 |
| Total | 8 | $4,566 |
These figures are invented to show how to read the sheet; they are not a benchmark. In this illustration the first-pick email carries the year: five stays averaging $630. If those had been marketplace bookings at 15%, the commission avoided is $472.50 on that email alone. Compare the total with the roughly $175 of time and any tool fee, and decide whether to keep the broadcasts or sharpen them. Emails 1 and 2 will show no revenue; judge them by replies, and by whether the people who got them rebook more often than those who did not.
The click should land somewhere that can take the booking. If your only option is "reply to this email", that is fine for the first year. When it stops being fine, this plan for a direct-booking holiday let website covers the calendar, payment and returning-guest offer.
Three slips that cost goodwill
The next three are invented, but each follows a pattern that is easy to fall into.
Emailing the whole export. An owner downloads every guest from the booking system, marketplace guests included, and sends a "we'd love to see you again" email. A few reply with surprise, one reports it to the marketplace, and the owner has risked a listing to save an hour. The cure is the how_booked column: filter it before every send.
The permanent code. Every email carries 10% off, so guests learn that waiting is rewarded and the "first pick" offer stops meaning anything. Alternate: one email with an extra, one with a dated discount, one with just news.
The confident wrong detail. An AI-written "we hope the hot tub was a treat" goes to guests who stayed in the cottage without one. Personalise only from fields in the sheet, have the assistant list which fields it used, and read the draft against the row before sending. For turning older, lapsed guests back into bookers, the general method in this tutorial on winning back lapsed customers is a useful companion.
Past-guest email questions from cottage owners
Can I email guests who booked through Airbnb?
Airbnb's terms say you may only use another member's personal information as necessary to facilitate a transaction, and they bar commercial messages to members without express consent. Having an address does not make someone a subscriber. Keep marketplace guests inside the marketplace's messaging unless they have told you they want your emails, and check which edition of the terms applies to you.
How often should I email past guests?
For one or two cottages, six or seven emails a year is a sensible ceiling, and never two in one week. The personal emails are triggered by a stay, so they spread themselves out. If more than one or two people unsubscribe after a send, the email was too frequent, too salesy or sent to the wrong segment.
What can I offer instead of a discount?
First pick of dates costs nothing but a short hold on your diary. A welcome hamper, a late checkout or a dinner booking made on their behalf costs far less than a discount and leaves your rate intact. Keep percentage discounts for midweek dates that would otherwise stay empty, and put an end date on every offer.
What if a guest replies asking to book direct?
If they booked direct, answer and take the booking. If they first booked through a marketplace, read that marketplace's terms before agreeing anything outside it; Airbnb's, for example, bar accepting bookings or payments outside the platform. When in doubt, ask the platform's support team and keep the reply friendly and factual.
Further reads
- Hotel Email Marketing With AI: Past-Guest Segments and Subject Lines — The hotel version: segments and subject lines to test
- Email Marketing Tools With AI: What a Small List Costs per Month — What a small list really costs on each email tool
- Airbnb Upselling: Early Check-In, Late Checkout and Extras With AI — Extras to offer that protect your nightly rate
- How Independent Hotels Win More Direct Bookings With AI — How larger independents win direct bookings
- How to Respond to Airbnb Reviews With AI: Glowing, Mixed, Bad — Reply to reviews that your emails will lean on
- AI Marketing Automation for Small Businesses: Chocolate Gift Seasons — One chocolate gift-box line taken through Easter, Mother's Day and Christmas, with pre-order reminders, cut-offs and shelf-life labels automated.
- AI Tools and AI Development: The Complete 2026 Guide — the AI hub, including every tutorial in the AI-for-business series.
Sources: Airbnb Terms of Service (section 11.1 and 5.4, edition last updated 5 February 2026), MailerLite pricing page, Brevo pricing page, Mailchimp pricing as listed in October 2026, Google's email sender guidelines.