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Category: Guest Communication
By: Megan O'Connor
Reply by Jake Anderson:
Here's my exact Hospitable (https://hospitable.com) sequence: 1. **Booking confirmed** (immediate): "Thanks for booking [property]! I'm [name] and I'll be your host. I'll send check-in details closer to your arrival. In the meantime, feel free to message me with any questions." 2. **3 days before check-in**: Full guidebook link with property info, local recommendations, house rules recap. 3. **Day of check-in, 2 hours before**: Check-in instructions with smart lock code, parking info, and step-by-step photos. "Your place is ready! Here's how to get in..." 4. **Evening of check-in** (8pm): "Hope you're settling in! Just checking — is everything OK? Let me know if you need anything." 5. **Night before checkout**: "Hope you're enjoying your stay! Just a reminder — checkout is at [time]. [Checkout instructions]. Safe travels!" 6. **Day after checkout**: "Thanks for staying! If you enjoyed your experience, I'd really appreciate a review. It helps future guests find us!" The mid-stay check-in (#4) is the secret weapon. It catches problems BEFORE they become bad reviews. About 10% of the time, a guest mentions something minor ("the shower drain is slow") that I can fix immediately via my handyman. Without that message, it would've been a review complaint.
Reply by Maria Gonzales:
My sequence is almost identical but I add one more: a **mid-stay message on day 3** for stays of 5+ nights. Something like "Hope you're having a great time! Here are a few local events happening this week..." — it keeps engagement up for longer stays and shows you're attentive without being overbearing. I also use the house manual generator at https://strspecialist.com/tools/house-manual-generator for the guidebook link in message #2. Cleaner than sending a PDF and guests actually read it on mobile.