TL;DR: A guesthouse needs about five emails a year for past guests: a thank-you after checkout, then four seasonal invitations, each sent before your guests' booking window for that season opens. Every email links to your own booking page and states one direct-booking benefit. Send them only to guests who agreed, ask every guest for a review in the same way, and keep urgency true.
A guesthouse has a list of eight hundred past guests in its property management system. Two years ago the owner sent a newsletter to all of them, with twelve photos and three offers. A few people booked; more unsubscribed. Since then, nothing. The list is still there, and every one of those guests now books through an OTA when they come back to the area.
What emails should a guesthouse send past guests to book direct? Fewer than most newsletters, timed better, and each with one clear invitation. This article gives a year-round sequence with send dates and wordings. It is part of our boutique hotel marketing strategy guide.
Why email past guests at all?
Because a past guest who books direct costs no commission, and email is the one channel to them that you own. Social media reaches whoever the platform chooses; an OTA message reaches them only while the booking lasts. A short, well-timed email reaches the guest when they are planning, if they agreed to hear from you.
Permission comes first. Ask at checkout or in the booking form, record the yes with the date in your PMS or guest list, and send marketing emails only to those guests. Each email needs an easy unsubscribe link. Your data-protection rules decide the details; check them before the first send.
The list grows with every stay. If you invite OTA guests to stay in touch during their visit, as described in getting the second stay direct, each season adds to the people this sequence can reach.
Which emails belong in the sequence?
Five a year is enough for most small properties: one after the stay, and one before each season's booking window opens. Each email has one purpose, one offer or reason to visit, and one link to your own booking page. More emails than that tend to raise unsubscribes faster than bookings.
| When | Purpose | Content | |
|---|---|---|---|
| 1. Thank-you | 1–2 days after checkout | Close the stay, open the door | A specific detail, the booking link, a review request asked of every guest |
| 2. Spring | Before the spring booking window | Fill shoulder weeks | A reason to visit, a direct benefit, dates |
| 3. Summer | Early in the year | First choice of rooms for returning guests | No discount; room choice, arrival tips |
| 4. Autumn | Before the autumn booking window | Fill the second shoulder season | Harvest, walks, a two-night offer |
| 5. Winter | Before the low season | Quiet weeks, longer stays | A weekly rate, a remote-work or rest week |
Summer is different on purpose. Demand peaks without help: about 31% of all EU tourist-accommodation nights in 2025 fell in July and August, according to Eurostat data (EU Transition Pathways, citing Eurostat). The summer email offers returning guests first choice of rooms, not a lower price.
When should each email go out?
Before your guests decide, which means weeks ahead of the season, not at its start. Take your own average booking window for that season from your PMS, add a week for the guest to read and plan, and count back from the first date you want to fill. Put each send date in your calendar for the whole year.
As a starting point before you have your own figure: Cloudbeds, a hotel-software vendor, reports from its own booking data that guests booked on average 40 days ahead in 2025, with North America at 48 and EMEA at 47 days (Cloudbeds). Those are averages across many property types. Returning guests who plan a regular trip may book much earlier.
The formula: send date = first arrival date to fill − your average booking window − 7 days. The seasonal plan that sets those arrival dates is in boutique hotel marketing plan.
Example (illustrative, not a real case): a ten-room guesthouse has 380 past guests who agreed to hear from it. Its PMS shows an average booking window of 50 days for autumn stays. The owner wants to fill from 25 September, so she counts back 50 days and then 7 more, and sends the autumn email on 30 July. The subject line: "The vineyard walk reopens in late September." The body has three sentences, the dates, the direct benefit, two nights with a tasting at a neighbouring winery, and one link to her booking page. After a month she counts 11 direct bookings from the email's tagged link, and 4 unsubscribes.
What should each email say?
One reason to come, one benefit of booking direct, one link. Write it like a note from the owner, not a brochure: short paragraphs, a real detail of the place, and the dates. Avoid invented urgency and anything that looks like a review incentive, because both damage trust and can break platform or consumer rules.
A template for the seasonal emails:
Subject: [The reason, in a few words] Hello [first name], [one sentence on what happens at the house or in the area that season]. If you would like to come back, [the direct benefit] when you book on our site: [booking link]. [Dates or minimum stay, and the cancellation terms in one line.] Warm regards, [owner's name]
Two rules keep the sequence clean. First, urgency must be true. After a UK Competition and Markets Authority probe, six booking sites committed not to create false scarcity or pressure (CMA, 2019); "only two rooms left" belongs in an email only if it is true on the day you send it. Second, review requests must not come with a reward. Google removes reviews paid for "directly or in kind", bans discounts or free services in exchange for reviews, and bars selectively soliciting positive reviews (Google Maps contribution policy). The US FTC rule of 2024 bans incentives conditioned on a review's sentiment (FTC, 2024).
So the review request in the thank-you email goes to every guest, in the same words, with nothing attached: "If you have a moment, we would be glad of a review, whatever you thought of the stay."
How do you know the sequence works?
Count direct bookings from each email, not opens. Give every email its own tagged link so that your booking engine records the source, and write down three numbers after each send: bookings and room-nights from the link, unsubscribes, and replies. After a year you know which season's email earns its place.
Look at the unsubscribes as a signal, not a failure. A few after each send is normal. A jump after one email usually means it was too long, too frequent or sent to people who never agreed. Check the consent records before the next send.
Use AI where it saves time: a draft of each seasonal email from your template and a brief, a German or English version for guests who wrote to you in those languages, and a shorter subject line. Read every draft, fix the facts, and send it yourself.
Action plan
The sequence takes one afternoon to set up for the whole year, and about an hour per email after that. Set the send dates first, because they drive everything else. Then write the template once and adapt it for each season, rather than writing five emails from scratch.
- Check your consent records and export the list of past guests who agreed.
- Find your average booking window per season in your PMS.
- Calculate the five send dates with the formula and put them in your calendar.
- Write the thank-you email and the seasonal template.
- Create a tagged booking link for each email.
- After each send, record bookings, room-nights, unsubscribes and replies.
If you want help writing seasonal emails and guest messages that sound like you and bring guests back to your own site, we are building the Conversion Copywriting Pack. Get notified when it launches.
FAQ
How many emails a year should a guesthouse send to past guests?
For most small properties about five is enough: a thank-you after each stay and one before each season's booking window. Each should have one purpose and one link to your booking page. Sending more often tends to raise unsubscribes faster than bookings, and the list is worth more than any single campaign.
Should the emails offer a discount?
Not necessarily. A direct-booking benefit, such as choosing the room, breakfast, a late checkout or a tasting with a local partner, often works as well and keeps your rates intact. Keep any price difference within your OTA contract, and for summer, when demand is high, offer returning guests first choice of rooms instead.
Can I email guests who booked through an OTA?
Only if you have their own email address and their permission to send marketing emails, and only within your OTA's terms. The simplest route is to ask in person during the stay whether they would like to hear about the next season, and record their yes with the date. Then they join the same sequence.
Can I ask for a review in the thank-you email?
Yes, as long as you ask every guest in the same way and attach no reward. Google bans discounts or free services in exchange for reviews and bars selectively asking only happy guests. A short line asking for a review whatever they thought of the stay keeps you within those rules.
Sources
- Tourism still peaks in July and August, Eurostat data show — European Commission, EU Transition Pathways, citing Eurostat, 2026.
- 2026 State of Independent Hotels Report — Cloudbeds (vendor booking data), 2026.
- Hotel booking sites to make major changes after CMA probe — UK Competition and Markets Authority, 2019.
- Fake engagement and conflict of interest — Google Maps contribution policy, accessed 2026.
- FTC announces final rule banning fake reviews and testimonials — U.S. Federal Trade Commission, 2024.