Guest experience
Pre-arrival emails guests actually read
The three emails every booking should trigger, what belongs in each, and how the right pre-arrival message empties your phone line in July.
2 min read

Count the questions you answer by phone in July. What time can we arrive? Is there a shop? Which gate do we use? Do you have wifi? Almost every one of them was asked by someone who already booked, which means almost every one of them could have been answered by an email you wrote once, in February.
A good email sequence is the highest-leverage hour of writing in this industry. Here is the three-email version that works.
Email one: the confirmation (instantly)
The confirmation has one job: prove the booking exists and remove doubt. Send it the moment the booking is made, automatically. It needs:
- Dates, pitch type, party size and the total paid or due.
- Your cancellation terms, stated plainly.
- A booking reference and a way to amend the booking.
- One warm sentence. "We're looking forward to having you" costs nothing and sets the tone.
Keep it short. Nobody reads a confirmation twice, so the practical details belong in the next one.
Email two: the pre-arrival brief (5 to 7 days before)
This is the email that empties your phone line, timed for when the trip becomes real and the questions start forming. Answer, in this order, the things guests actually ask:
- Arrival and departure times, and what to do if they will be late.
- Exact directions, including the "ignore the satnav at the church" paragraph every rural site needs, and a what3words or pin for the entrance.
- What happens on arrival. Where to stop, where reception is, what happens after hours.
- What to bring and what not to. Hook-up lead length, whether you sell gas, firewood rules, BBQ policy.
- The local essentials. Nearest supermarket, cash machine, fuel, and your two favourite pubs. Guests trust a short opinionated list far more than a tourism brochure.
- The weather-proofing paragraph. A gentle note that the forecast changes hourly on the coast prevents the ritual Thursday cancellation panic.
Write it once in your own voice, read it aloud, and cut a third. It should feel like a knowledgeable friend, not a terms and conditions annex.
Email three: the welcome-back (day after departure)
The cheapest marketing you will ever do:
- Thank them for coming.
- Ask for a review, with a direct link, while the holiday glow lasts. More on timing in our review playbook.
- Tell them when next season's booking opens, and consider giving returning guests first pick.
One email, three sentences, sent automatically. It quietly builds the returning-guest base that makes direct bookings compound.
Make the system do the sending
None of this works if a human has to remember to send it. The whole point is that every booking, whether it came from your page, the phone or a listing site, triggers the same sequence at the same times. That is exactly what Pillowcase's automatic guest emails do, branded for your site, with your words.
Whatever system sends yours: write them once, read them as a guest would, and then enjoy the sound of a phone that does not ring.

