Upselling gap and bookend nights
Upselling is the practice of offering extensions or add-ons to existing reservations to drive a better return.
Common upsells include gap night or bookend extensions. These can be very lucrative, as all of your fixed reservation costs have been accounted for (like linen), so even one extra night can move the ROI by a percent or two.
With our new AI-driven upsell system, we can proactively offer these in a very conversational manner, but without our team doing this manually. Our platform automatically identifies opportunities within existing reservations and offers guests tailored upgrades at just the right time. We want to work collaboratively with owners at agree a discounted rate for these extra nights, as is standard in the short-term rental market.
Why It Matters… and what the benefits are
• Grow your income without adding more bookings. You can increase revenue directly from the guests you already have. Owners who collaborate on upsells typically see 10–20% more revenue per booking—without extra workload or staffing.
• Better guest experience, higher satisfaction. Guests appreciate the convenience and personal touch of smart, well-timed offers. Both guest reviews and repeat/return guest numbers are elevated.
How it works
Our AI agent, Besty, has a smart upselling feature called book-end days. It looks for empty nights directly before or after a guest’s existing booking. If those nights are still unbooked five days before arrival, Besty automatically offers them to the guest at a discounted rate. We exclude weekends and public holidays and event days, so you will never be locked out of a more suitable booking on those high-revenue nights.
This helps in two ways:
Guests get the chance to extend their stay at a great price, which is convenient for them.
You fill gaps in your calendar that might otherwise sit empty, increasing your overall rental revenue.
It’s a gentle, automated upsell — not pushy — and it only triggers when it makes sense for both the property, the guest, and the Groundswell Team. We can set the upsell discount anywhere in that 40–60% range, depending on what suits you best. Please let us know which discount level you’d prefer to offer.