Gap night upsells
Two nights between bookings? Offer them to guests who already chose your rental.
One guest leaves on Friday; the next arrives on Sunday. Before finding a new two-night booking, you can ask the departing guest to stay longer or the arriving guest to come sooner. The offer starts with available dates and a stay that is already planned.
That is a gap night upsell for vacation rentals. Rentevo identifies gaps between bookings, prepares an offer with dates and a price, and sends it through WhatsApp or your PMS conversations. You set the rules and confirm the booking change when the guest accepts.
One gap in the calendar, two possible offers
Illustrative example: these dates and availability do not come from a real property.
Previous stay
The guest leaves on Friday
Two available nights
Friday to Sunday
Next stay
The next guest arrives on Sunday
Offer the departing guest a stay until Sunday. Offer the arriving guest a Friday start instead. In Rentevo, you can choose to contact one guest or both in your upsell settings.
These offers cover additional nights, with dates and a price for that period. An arrival a few hours early or a later checkout on the same day is a separate request for your team to assess.
From your calendar to a clear guest offer
The Upsell section lists gaps between confirmed reservations alongside your calendar. Select an opportunity and generate a preview: Rentevo rechecks availability and pricing before preparing the message. You can see the rental, the extra dates and the total for the entire period.
The price comes from the PMS connected to the property. You can set an increase or a discount as a percentage or fixed amount, with different rules by booking platform. The offer uses your rates and your pricing choices, so the assistant does not have to invent a quote.
Connect OctorateConnect LodgifyChoose when to offer extra nights and where to send them
Automatic upsells are available with Octorate and Lodgify. Start with a preview and send an offer manually, or configure automatic delivery: when a new booking is detected, a chosen number of days before the gap, or after the guest’s scheduled arrival. You also choose the gap lengths to consider and how long guests have to respond.
For Airbnb, Booking.com and other reservations, choose WhatsApp, the Channel Manager conversation or both. WhatsApp offers use approved templates on your connected number; PMS offers appear in the reservation’s conversation.
WhatsApp for your guestsThe guest is interested. What happens next?
When an offer is accepted, Rentevo records the outcome and creates a To-do for your team to confirm it. If both guests received the offer, the first acceptance claims the opportunity and competing offers are superseded. Your team checks and updates the booking in the PMS: Rentevo does not automatically change the reservation or collect payment for the extension.
For a WhatsApp offer covering one period, “I’m interested” and “No thanks” buttons record the guest’s response. If the guest asks a question or needs to choose between periods, the conversation continues to clarify what they want. History shows sends, acceptances and errors, with manual and automatic offers kept distinct.
Follow conversations with your teamTry the guest assistant
Ask about arrival times, property instructions or parking in the interactive demo. It uses a sample property to let you try a conversation. In a guided demo, we can also show you the calendar, offer previews and the extra-night workflow.
Test your offers before sending them to guests
Connect your PMS, review a real calendar gap and prepare the templates. Upsell Test Mode simulates offers and records the results without contacting guests, on both WhatsApp and the Channel Manager. When the dates, prices and messages are right, switch to live sends. This control is separate from AI reply Test Mode.
Test Mode and human control in RentevoRentevo offers a 15-day trial. Pricing is €9 per property per month, including VAT, for up to 10 properties; larger portfolios receive custom pricing. Meta charges for paid WhatsApp messages are additional. Bring a calendar gap to the demo and we can walk through a concrete offer.
See Rentevo pricingQuestions about extra-night offers
Can I offer extra nights without WhatsApp?
Yes. With Octorate and Lodgify, you can use PMS conversations. Choose the channel in Upsell settings and prepare your offer content; this workflow does not require a WhatsApp number.
Does accepting an offer automatically extend the booking?
No. Acceptance creates a To-do for your team. You confirm the extension, update the stay in your PMS and handle payment through your usual process.
Do I have to discount a stay extension?
No. The starting price comes from the PMS for the offered nights. Keep that price or apply an increase or discount through your settings.