"Automatically reach out to guests to extend their stays." It finds nights you have not sold that sit next to a booking you have, and offers them to the guest at a discount.

Find it in the Booking Booster section of Settings, then Upsells. Remember that this section has its own Save, separate from every other block on that page.

Two options, and the product's own descriptions are worth quoting because they contain the recommendation.

Bookend nights, the recommended setting: "Message each guest individually. Offer a discount to extend their stay on any available nights on either end of their trip."

Orphan nights: "Message both guests with a discounted offer whenever there is a gap between their bookings. (This is less effective because it requires a gap between two bookings, as opposed to taking advantage of unused nights on either end of a booking. Note that if you select 'bookend' above, it will do everything that 'Orphan Nights' does, plus more.)"

That last sentence settles it. Bookend is a superset of orphan. There is no scenario where orphan alone captures something bookend misses, so unless you have a specific reason, choose bookend.

Maximum number of nights to offer caps the extension at either end, and the UI gives a worked example: "if you enter 2, Besty will offer to extend the guest's stay by 1 or 2 nights, both before and after their trip, only using available nights."

Most accounts keep this at one or two. Offering longer extensions tends to give away nights you would have sold at full rate anyway.

Which nights restricts it to all nights or a selection, useful if you would rather not discount weekends. Nightly discount is the percentage off.

Be deliberate about the discount. It applies to real bookings and it cannot be set to zero, so switching Booking Booster on is a commitment to discounting inventory that might otherwise have sold. Twenty to thirty percent is a common range, and it is a margin decision rather than a technical setting.

Three independent timing rules sit under When to send offers, and each is disabled by setting it to 0:

The latest-day rule is worth setting if extra nights create work for your cleaning team at short notice.

Restrict to channels limits the whole programme to selected booking channels.

Further down the page, Calculating price for upsells asks how Besty should work out the base nightly rate, with two options that are both labelled with your connected PMS: the accommodation total divided by the number of nights, or the gross revenue divided by the number of nights.

The option labels differ by PMS, so what you see depends on what you are connected to. The difference matters, because one figure may include taxes and fees and the other may not, which changes every discounted price Besty quotes.

Booking Booster works from your rate and does not automatically add taxes and fees on top. There is a wording setting on the same page that tells guests taxes and fees will be applied to any stated price, which does not apply to Airbnb upsells because those require an exact quote.

If your upsell totals have not matched what a guest was quoted, check the tax rate on the listing under Portfolio, then Listings, then Upsell Fees. An unconfigured rate there is the usual cause.

Booking Booster on Airbnb always uses alteration requests, because extending dates on Airbnb requires one. That is true even if you have enabled off-platform Airbnb upsells for early check-in and late check-out.

Reach out via chat or at support@getbesty.ai.