Upselling Engine
TurnEveryEmptyNightandEarlyArrivalIntoFoundRevenue
Besty automates upselling end-to-end - gap-night offers, early check-in and late checkout pricing, conversational selling inside message threads, Airbnb-compliant payments, and automatic PMS updates.
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Booking Booster
Orphan Nights Cost You Thousands. Booking Booster Recovers Them.
Besty scans every calendar for gap nights and bookend openings, then sends discounted offers to the right guest at the right time. Average 15% conversion rate, routinely generating 3x the subscription cost in found revenue.
Booking Booster Config
Gap Night Settings
Gap mode
Message each guest individually to extend their stay before or after
Nightly discount
15%Send offers on
Typical results
15%
conversion rate
3x
subscription ROI
Scans every calendar for orphan nights and bookend gaps automatically
Configurable discount percentages, timing windows, and day-of-week rules
Guests receive a direct link to shop and purchase available extra nights
Works out of the box across all listings with no per-property setup
Conversions tracked in real-time ROI dashboard with payment status
Time-Based Pricing
Price Every Extra Hour. Protect Every Turnaround.
Tiered pricing for early check-ins and late checkouts - by hours, as a percentage of the nightly rate or flat dollar amounts. Besty only offers when availability allows and automatically blocks the calendar when guests purchase.
Besty messages guests 24 hours ahead with pricing options
Besty messages guests 24 hours ahead with pricing options
Back-to-back conflict detection
Offers are only sent when availability allows. If another guest checks in that day, early check-in stays off the table.
Automatic calendar blocking
When a guest buys an extension, Besty blocks the night before (or after) on the calendar to protect the next reservation.
Policy windows
Control earliest acceptance time, latest acceptance time, and day-of-week restrictions for each upsell type.
Conversational Selling
Upsell Inside the Conversation Where the Guest Already Lives
Besty sends proactive offers at configured times and reacts mid-conversation when a guest asks to extend or check in early - responding with specific dates, prices, and a purchase link. For requests that can't be confirmed yet, Besty runs a presale.
Kristy - Perla 61
Mar 29 – Apr 2, 2026
Besty detects intent and responds with pricing + purchase link in the same thread
Presale Workflow
Capture intent now, charge when confirmed
Guest asks
"Can I check in early?"
Back-to-back conflict
Can't confirm yet
Presale captured
Intent + payment auth held
Availability confirmed
Previous guest checks out
Auto-charged
Guest notified, PMS updated
No separate app, no clunky one-way blasts - everything in the conversation
How it works
Proactive offers fire at configured times. Reactive responses trigger mid-thread when a guest mentions early arrival, late departure, or extra nights.
Payments & Sync
Collect Payment. Update the PMS. Zero Manual Steps.
Stripe for direct bookings, Airbnb Resolution Center for platform-compliant upsells. After purchase, Besty automatically updates reservation dates, check-in times, messaging schedules, lock code delivery, and optional calendar blocks.
Direct Bookings via Stripe
Guests receive a secure checkout link. Payment processes through your connected Stripe account with automatic receipts and reconciliation.
Airbnb via Resolution Center
Besty guides guests through the "send money → extra services" flow without violating platform rules. Detects payment confirmations from Airbnb notifications and verifies amounts match.
Payment captured
$84.29 via Stripe
Reservation dates updated
Checkout extended to Apr 5
Check-in/out times adjusted
Late checkout: 12:00 PM
Messaging schedule shifted
Departure messages rescheduled
Lock code delivery updated
Access extended to new checkout
All updates happen automatically - no manual PMS changes needed
Custom Upsells & Blackout Dates
Sell Anything. Protect Peak Pricing Automatically.
Beyond time-based extensions - sell pet fees, pool heating, horseback riding, affiliate experiences, and anything else your guests want. Blackout dates exclude specific months or holidays to protect peak pricing and prevent guest fatigue.
Club Room Rental
Host your next event in our spacious Big Club Room
Pets
Pets are welcome at this property for an additional fee of $20 per night
Friday-Sunday Parking Fee
Please make sure you send us your car plate number
Conference Room
Need a professional space? Our Conference Room is available at just $40/hour
Holiday Exceptions
Disable early check-in, late checkout, and booking booster on these days
Offer modes
Proactive
Appear in the guest upsell portal automatically
Reactive
Only offered when a guest specifically asks
At a glance
Revenue that finds itself while you focus on hospitality
$104K+
Tracked upsell revenue across a single portfolio
15%
Average conversion rate on Booking Booster gap-night offers
Zero
Manual steps from offer to payment to PMS update
Book a demo
Book a demo today to learn more about Upselling Engine
Join hundreds of vacation rental operators using Besty to earn more from every booking automatically.