How do I get guests to pay before check-in without chasing them?
Take a deposit at booking, let the balance collect itself before arrival, and stop chasing payments over email. Here's the two-payment setup I use on our Cape Cod place.
Split the payment in two. Take a deposit of 25-50% at booking to hold the dates, then set the balance to collect on its own a set number of days before check-in, with 14 days a safe default. Reminders and card-failure notices go out automatically, so the guest arrives already paid and you never send a single follow-up email.
- A 25-50% deposit at booking holds the dates and gives you a real commitment, not a maybe.
- The balance collects itself before arrival. Pick a number of days out; 14 is safe, 14-30 is the common range.
- Reminders send on their own, so chasing payments stops being your job.
- A failed card turns into a heads-up weeks in advance, not a scramble at the front door.
- By check-in the guest owes you nothing, and you never had to ask twice.
Why split the payment into a deposit and a balance?
For years we took the whole week up front, or we tried to. Some guests paid right away. Others sat on it, and I'd end up sending a note two weeks before their trip asking where the money was. That's an awkward email to write to someone about to sleep in your house.
Splitting it fixes both ends. The deposit at booking means the person actually intends to come. The balance later means they aren't handing over $2,400 for a trip that's five months out. And you set the timing once, so neither payment lands on your to-do list again.
The deposit is 25-50% of the total. I use 30%. Below 25% and a cancellation costs you more than the guest; above 50% and people hesitate to book that far ahead. Somewhere in that band is the sweet spot, and it depends on how nervous you are about empty weeks.
When should the balance collect automatically?
You pick a number of days before check-in, and the balance charges itself on that day. 14 days is a safe default. Most owners land somewhere in the 14-30 day range.
The reason to leave room is card trouble. If the balance runs 14 days out and a card gets declined, the guest still has two weeks to fix it. Push it closer to arrival and a bad card becomes your problem on a Friday afternoon.
- Guest booksDeposit charged, dates held
- 14 days outBalance collects automatically
- Card failsGuest asked to update, with time to spare
- Check-inNothing owed, nothing to chase
Do I have to remind guests to pay?
No. That's the part that changed the most for me. The reminders go out on their own before the balance is due, and if a charge doesn't go through, the guest gets asked to update the card without me touching anything.
So the failed card, the thing that used to mean a phone call, is now a message the guest sees on their own, weeks early, while there's still plenty of time. I find out it happened and that it got sorted, usually in the same breath.
A real booking on our place. A week runs $2,400. At booking, the guest pays a 30% deposit, so $720 comes in and the dates are locked. Fourteen days before check-in, the remaining $1,680 collects on its own. Card processing runs about 2.9% + $0.30 per charge, and that's the only cut. By the time they pull into the driveway, the full $2,400 is settled and I never sent a payment reminder.
How do I set this up so it runs itself?
- 1Pick your depositSet it between 25% and 50% of the booking total. If you're unsure, 30% is a fine place to start.
- 2Choose your balance timingDecide how many days before check-in the balance should collect. Use 14 if you want a safe default, or anywhere in the 14-30 day range.
- 3Send the booking linkThe guest pays the deposit to confirm. The dates are held the moment that clears.
- 4Let it runThe balance charges itself on the day you set. Reminders and any card-update requests go out automatically. You do nothing until the guest arrives, already paid.
What does collecting payments this way cost me?
Card processing is about 2.9% on each charge, whoever you use. That part is the same everywhere. The difference is what sits on top of it.
List on a big platform and they add roughly 14% to what the guest pays, then take about 3% from you on the way out. Take the booking directly and none of that applies. On Downwind it's a flat $20/month, no matter how many weeks you book, plus the card fee you'd pay anywhere.
| On a $2,400 week | Platform | Direct with Downwind |
|---|---|---|
| Guest pays | About $2,736 (14% added) | $2,400 |
| Platform's cut from you | About 3% ($72) | None |
| Card processing | About 2.9% | About 2.9% |
| Your fixed cost | $0 | $20/month, all bookings |
The best payment reminder is the one you never had to send.
Frequently asked questions
What if the guest's card fails when the balance is due?
They're asked to update it automatically, and because the balance runs days before check-in, there's time to fix it well before arrival. A bad card becomes a small heads-up in advance instead of a problem at the door.
How big should the deposit be?
Between 25% and 50% of the total. Under 25% and a cancellation costs you more than the guest; over 50% and people hesitate to commit months out. 30% is a solid middle.
How many days before check-in should I collect the balance?
14 days is a safe default, and 14-30 days is the common range. Leaving two weeks or more gives a guest time to sort out a declined card before they travel.
Do I have to send the reminders myself?
No. Reminders and card-update requests send on their own. You set the deposit and the balance timing once, and the rest happens without you touching it.
Will the guest owe anything at check-in?
No. The deposit clears at booking and the balance collects before arrival, so by the time they show up the full amount is paid and there's nothing to settle in person.
Collect your first direct payment.
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