Oh yes! And if we can preset a discount for the extension would be mind blowing

Guests often consider extending their stays, especially if nearby dates are open. This feature would automatically detect when the check-in day minus one or the check-out day plus one is available, and then send a customizable message encouraging guests to book those dates.

Example Use Case:

A guest books June 10–12.

The nights of June 9 and June 13 are unbooked.

The system automatically sends:

“Hi [Guest Name], the night before and after your stay are still available if you’d like to extend your visit. Let us know if you’re interested!”

This feature would add tens of thousands of dollars im revenue per year for use while cutting huge amounts of waste spent manually sending these emails.

It would be extremely useful, and some places like breezeway and charge automation are already offering it as an add on. Basically an upsell like early check-in, or late checkout that is only offered if there is a gap night.

This is along the lines of "if" "then" messaging or "and" "or" messaging. example: If the room is open on the calendar then we will trigger a message that offers the guest an extra day at a discount.

YES PLEASE

I cannot believe this is not a feature. This is basic and I assumed was a part of any functioning PMS ...even Guesty For Hosts has this.

This would allow for a lot of new messaging triggers and potential revenue streams. Please implement soon!

We had this feature at Guesty and was a great boost to get more direct-bookings on sundays. more money for hostfully, more money for us. easy fix

This is a feature available on Hospitable and would love to be able to use it here. We need the ability to add a condition to a complex trigger that will check the calendar to see if there are vacant days before or after a guest booking. I'd like to send a message offering to add a discounted day to their reservation before or after their stay but don't want to send the message if the day isn't available.

Airbnb's calendar feature as an example

Identify impacted availability due to gap nights affected by minimum night rule and make these dates automatically available

I would like to have the option to set a trigger for orphan days when a guest booked and a week before or so, the system detects that there's an orphan day so I can offer this automatically to guests.

This would be great so we can maximize revenue and book up calendars more! A lot of PMS is already doing this!

Send triggers that allow you to create a email you can send out to add a early check in or even an extra day based on calendar availability, For Ex: if an extra day is available at the end of a reservation 2 days before the reservation ends, I can send out an email that lets them at a day at a discounted rate to help book the calendar up, same goes for early and late checkouts and they can pay automatically and it adds the info to their reservation

I would like to see gap night messaging triggers like some other PMS have. This will significantly help increase revenue and eliminate gap nights or orphan days.

For example, if a guest books and it creates an orphan day or gap night in between 2 bookings, the system will automatically pick up and trigger a templated message offering for the guest before/after to add that additional night (or two, depending on your customizable threshold) and invite them to add it on so we can maximize occupancy and REVPAR.

Same goes for nights before stay

Trigger to offer additional nights before or after reservation dates

Or to offer early check-in

Absolutely! this can generate a lot of revenue for me and is a real gamechanger in managing gap days.

We are looking to send messages to our current guests when there are additional nights available at the property they are staying at. In order to automate this process we would need a trigger that sends the message 1 day before check out if the property is available for the guest to extend their stay.

+1 on this. Very important sales tool I need to implement like yesterday