AI Guest Upsells: Turn Gap Nights Into Revenue for Airbnb Hosts
Boring Host works 24/7 to find and capture upsell opportunities on autopilot.
Cut down 40% of your phone calls to front desk
Many guests still prefer to call, especially during check-in and late at night. Boring Host acts like an AI phone answering agent for vacation rentals, it resolves common questions and escalates complex cases to your team with a summary.
Fill more rooms
Free up popular inventory for last-minute-guests throughout smart upgrades.
Charge for late checkouts
Automatically capture payment from guests who want extra time in their room.
Offer early check-in
Offer upsells early to prevent common guest questions.
How it works
Spots the opportunity
When a booking comes in, Boring Host checks the calendar for upsell windows: gap nights, early check-in availability, turnover timing. It also recognizes when a guest asks about things like “can we check in early?” in conversation.
Checks your rules first
Before offering anything, it looks at your calendar, turnover schedule, and property rules. If there’s a same-day turnover and no time for early check-in, it won’t offer it. No surprises for your cleaning team.
Sends the offer and collects payment
It messages the guest with a clear offer and price. If the guest accepts, Boring Host collects payment and confirms the booking change. No back-and-forth, no manual invoicing.
Notifies your team
After the upsell is confirmed, your team gets a summary: what was sold, what needs to happen (adjust cleaning schedule, prepare welcome package, etc.), and any follow-up steps.
Property managers experience results that make an impact
“Boring host has been a competitive advantage to our business across 100 units, from the instant responses to the add-on’s it has. It has changed the way we work, for the better.”
Steve Taggert
Managing Director – MyGetaways
Boring host runs itself, cutting 78% of our manual work.
5.4x
Return with revenue generated by AI upsells.
“It has been a game changer for our operation. Their product is great, and they’re building a community of operators around the world who want to leverage AI in their STR business.”
Dustin Gaspard
Founder – Lodgeful
89%
Guests prefer messaging, allowing us to meet them where it’s convenient
47%
Phone calls have been cut down to our front desk.
Built to give property managers their time back.
Here’s what our property managers needed to know before signing up
How much extra revenue can I expect from upsells?
Most hosts who offer 3-4 upsells add $50-150 per booking in extra revenue. The exact amount depends on your property type, location, and guest profile. Beach properties and urban apartments tend to do best because guests are already in spending mode.
Does Boring Host decide what to offer, or do I?
You set the rules. You choose which upsells to offer, set the prices, and define when they’re available. Boring Host handles the timing, messaging, and payment collection based on your preferences. You stay in control of the guest experience.
What if a guest asks for something that isn't available?
Boring Host checks your calendar and turnover schedule before making any offer. If early check-in isn’t possible because of a same-day turnover, it won’t offer it. If a guest asks directly, it explains why it’s not available and suggests an alternative when one exists.
Can I offer upsells on Airbnb, VRBO, and direct bookings?
Yes. Boring Host works across all your booking channels. The upsell offers go through your guest messaging (not through the OTA platform), so they work the same way regardless of where the booking came from.
Will upsell messages annoy my guests?
The messages are timed to feel helpful, not pushy. They go out at natural points in the guest journey (pre-arrival, mid-stay, checkout) and are phrased as options, not obligations. Guests who aren’t interested simply don’t respond. Most hosts find that guests appreciate being offered choices they didn’t know were available.
How do I set up my first upsell?
After connecting your PMS, you pick which upsells you want to offer, set pricing, and define availability rules. Boring Host starts offering them automatically on the next qualifying booking. Most hosts are live within 30 minutes.