Guest communication is where five-star stays are made or lost. Not the property itself — the communication before, during, and after the stay determines whether guests feel cared for or left to figure things out alone. In the Stratton market, where guests are often traveling from Boston or New York for a planned ski weekend, the quality of your communication directly affects reviews and repeat booking rates.

This is the communication framework that consistently produces positive outcomes.

Before the Stay: Three Touchpoints

1. Booking Confirmation (Immediate)

Send a booking confirmation immediately after the reservation is made. This isn't just an automated receipt — it's your first real communication as a host. What to include:

  • A warm, brief welcome line that feels personal, not automated
  • Confirmation of dates, property name, and total guests
  • A preview of what they can expect from you (you'll send detailed check-in info 48 hours before arrival)
  • An invitation to message with questions

Tone matters here. Guests are about to trust you with a meaningful portion of their vacation budget. A professional but human message sets the tone for the relationship. An automated template with no warmth signals that no one is paying attention.

2. Pre-Stay Information (48–72 Hours Before Check-In)

This is the most important message you'll send. Vermont ski guests are often arriving after a multi-hour drive from a major metro. They want to know exactly what to do when they get there, especially if they're arriving after dark in an unfamiliar area.

What to include in the pre-stay message:

  • Exact address and GPS note — Many Vermont properties are in areas where GPS takes guests to the wrong place. Include both the address AND directions from Route 30 or the nearest landmark.
  • Parking instructions — How many cars fit, where exactly to park, any restrictions. Snow in Vermont means parking spots can become unclear.
  • Door code or key pickup — The exact code, which door, and any quirks (the door sticks when it's cold, the lock requires a specific motion).
  • WiFi name and password — Print this in the house and put it in the message. Guests ask for this immediately upon arrival.
  • Hot tub instructions — How to turn it on, what temperature to expect, and any timing notes (it may take 30 minutes to reach temperature if it's been cooling).
  • Emergency contact — Your number and a backup. Something always comes up. Make reaching you easy.
  • Weather note — If there's a winter storm forecasted for their arrival or departure, a brief heads-up shows attentiveness and lets them plan. Check weather on their behalf.

Keep this message well-organized with clear headers or bullet points. Guests reference it on arrival, often from a phone while sitting in the driveway. Dense paragraphs don't work.

3. Day-of-Check-In Message

A brief check-in message on the day of arrival — usually mid-afternoon — confirms everything is ready and signals that you're available. One short paragraph:

"Your [property name] is ready for you. The hot tub is up to temperature and the fireplace has wood stocked. If you hit any trouble on arrival, I'm at [number]. Enjoy the weekend."

This message takes 30 seconds to send and gets mentioned in reviews more often than almost anything else you do.

During the Stay

Check-In Confirmation (Within 2 Hours of Arrival)

After guests would reasonably have arrived, send a brief message asking if they got in okay and if everything looks good. Don't wait for them to find a problem and report it — ask proactively. This catches issues early (before they stew into review material) and signals genuine attention.

"Hope the drive up was good — did everything go smoothly on check-in? Let me know if anything needs attention."

Mid-Stay Check-In (For 5+ Night Stays)

For stays of five nights or more, a mid-stay check-in around day 2 or 3 is worth doing. It's not intrusive — it's attentive. Many issues guests experience quietly (the oven is acting up, the hot tub lost temperature) get resolved before the guest leaves if you ask. They don't get resolved if you don't ask and they appear in the review instead.

Responding to Issues

Speed of response to in-stay issues is one of the highest-weighted factors in STR reviews. "The host responded immediately" appears in five-star reviews constantly. "It took hours to hear back" appears in three-star reviews.

For Vermont ski properties, the most common in-stay issues:

  • Hot tub temperature or water chemistry questions — have a FAQ ready or check proactively
  • Heating issues — know your HVAC system and have a local HVAC contact
  • WiFi connectivity — know your router reset process
  • TV and streaming setup — have instructions ready to send
  • Early morning departure logistics in a snowstorm — parking, plowing, road conditions

For anything you can't solve immediately, acknowledge the message and set a timeline. "I'm on it, give me 30 minutes and I'll have a solution." Silence is worse than any delay.

Post-Stay: Checkout and Review

Checkout Instructions (Night Before Checkout)

Send checkout instructions the evening before the guest's departure. Vermont ski guests often have a long drive home and are packing and organizing the night before. Clear, brief instructions:

  • Checkout time (and flexibility if you have it)
  • What to do with linens (leave on beds vs. strip and pile, depending on your cleaner's preference)
  • Dishes — run dishwasher or leave on counter?
  • Trash — where to leave it
  • Lock the door and note the code resets automatically
  • What to do with keys if you used physical keys

If there's a snowstorm forecasted for checkout morning, mention it proactively: "Roads are expecting 6 inches overnight — if you need to push checkout by an hour to wait for plowing, let me know and we'll make it work."

The Post-Checkout Message and Review Request

Send a farewell message within a few hours of checkout. Two sentences maximum:

"Hope you had a great time at [property] and a safe drive home. If everything was as expected, we'd love a review — it helps other guests find the property."

Keep the review ask soft. A hard sell ("Please leave us a 5-star review!") reads as desperate. A natural ask after a genuine sign-off reads as appropriate.

On Airbnb, you also write a guest review. Write it promptly and specifically — "A wonderful group of skiers, left the property in excellent condition, communicated clearly" beats "Great guests, would host again." Specific reviews get read; generic ones don't.

Template Library vs. Personal Touch

Having message templates for each touchpoint saves time and ensures consistency. But templates need to feel personal, not automated. The balance: use templates as a starting point, add one or two specific details per message (their names, a reference to the ski conditions that weekend, a note about the expected snowfall), and send.

Guests can tell when a message was written by a person who thought about them for 20 seconds. They can also tell when it's a mass-produced template. For Vermont ski guests booking a $3,000+ week, the latter communicates that you're not paying attention to them specifically. The former builds the kind of relationship that generates repeat bookings.

Response Time as Policy

Airbnb tracks your response time and rate. But more importantly, guests form impressions of your attentiveness based on how quickly you respond. The standard expectation in the current STR market is a response within 1 hour during normal waking hours. Faster is better; slower consistently hurts conversion and reviews.

For Vermont ski properties, peak inquiry periods are Thursday and Friday evenings as guests are checking conditions and finalizing weekend plans. Being available and responsive during these windows specifically can convert tentative inquiries into bookings that would otherwise go to a competitor who responded first.