Gap nights, or "Extend your stay" upsell offers, are one of the fastest ways to add revenue to stays you're already getting.
Enso Connect automatically surfaces these offers to your guests only when a gap is available, and promotes them with timed automated messages, so you never miss an opportunity without extra work.
What are gap nights?
A gap night is an unbooked night that sits between two reservations, either directly before a guest checks in, or directly after they check out. Instead of leaving it empty, you can offer the current guest the chance to extend their stay at a discount.
STEP 1 Set up the gap night offer in your Boarding Pass
Go to Boarding Pass config and open the Upsell bucket
Locate the Pre-Stay Extension and Post-Stay Extension templates. Click Use template
Add your offer copy. Frame it as an extension - something like "Stay longer for less" or "Enjoy one more night" works well
Set your discount. We recommend 20–30% off the nightly rate. If you're sending the offer close to check-in, you can go up to 50%
Choose whether to require manual approval or enable auto-approval. If the gap is confirmed available, auto-approval is safe and removes friction.
Tip: Offer 1, 2, and 3-night options where possible. More options means higher conversion. A guest who won't stay 3 extra nights may still take 1.
STEP 2 Activate the automated message workflow
The offer in your Boarding Pass alone won't drive conversions. The message is what triggers action.
Go to Message Automations → Pre-Check-In bucket
Find the Pre-Stay Gap Night template (or Post-Stay Gap Night for the checkout version). Click Use template and review the pre-built conditions.
Adjust the send timing to suit your business. The sweet spot is between booking confirmation and check-in. Too early and the guest may have booked the extra night anyway at full rate; too close to arrival and they've likely already made plans
Review the message copy and adjust to match your brand voice
Save and activate
Note: For Airbnb bookings, messages are sent via Airbnb and SMS. For all other channels (VRBO, Booking.com, direct), messages are sent via SMS and email, or OTA message if your PMS supports it.
PMS sync note: For direct bookings, most PMSs will update the reservation dates automatically. For OTA bookings (Airbnb, VRBO, Booking.com), date updates may not sync back to your PMS due to OTA restrictions - the updated dates will be reflected in Enso. If you're unsure about your specific PMS, contact support before going live.
Gap nights FAQs
What if I block dates in my PMS for cleaning or admin?
Enso looks at actual guest arrivals and departures, not calendar blocks, so those dates won't interfere with gap night detection.
Can a guest stack an early check-in with a gap night?
Yes - if a guest purchases an early check-in and a gap night extension, both will be reflected in Enso. The early check-in time carries over to the extended stay.
What if I don't want to collect payment through Enso?
You can set the upsell as a request (no price attached) and collect payment through your PMS instead. Your team is notified when a request comes in and can handle it manually. This also avoids any Enso platform fees.
Need help with your setup?
Book a call with the CS team → Our team can review your account configuration and make sure your gap night workflows are set up to convert.