I Analyzed 500 Guest Messages: What Travelers Actually Ask Before Check-In

The Question That Started It All

After hosting for several years across multiple properties, I found myself answering the same questions over and over again. So I did what any data-obsessed host would do. I went back through over 500 guest messages to categorize exactly what travelers were asking me before they checked in.

The results were eye-opening. Not because the questions were surprising, but because 87% of them could have been answered automatically with a well-organized digital guidebook. Here is what I learned.

The Top 10 Questions Guests Ask Before Check-In

After categorizing all 500+ messages, clear patterns emerged. Here are the questions I received most frequently, ranked by volume:

1. WiFi Information (23% of all questions)

This was the runaway winner. Nearly a quarter of all pre-check-in messages asked about WiFi. They wanted the network name, password, or to know if WiFi was even available. Guests want to know they will be connected the moment they walk in.

The Solution: Include WiFi details in your booking confirmation, check-in instructions, AND your digital guidebook. Make it impossible to miss. Better yet, create a WiFi QR code that connects devices automatically.

2. Check-In Time and Early Arrival (18%)

"Can we check in early?" "What if our flight arrives at 2pm?" "Is there somewhere to store luggage?" Guests are anxious about that awkward gap between arriving in town and being able to access your property.

The Solution: Be proactive. In your pre-arrival message, clearly state your check-in time and your policy on early arrivals. If you can offer flexibility, say so. If you cannot, explain why and offer alternatives (luggage storage, nearby coffee shops, etc.).

3. Parking Instructions (14%)

Where do I park? Is parking free? Do I need a permit? Can I fit a large vehicle? Parking anxiety is real, especially in urban areas or properties with shared lots.

The Solution: Include photos of your parking area with clear markings showing which spot(s) belong to guests. If street parking is required, provide specific instructions about permits, restrictions, and the best places to park.

4. Exact Location and Directions (11%)

Even with GPS, guests want confirmation they are in the right place. "Is there a gate code?" "Which building is yours?" "The GPS took me to the wrong address."

The Solution: Provide landmark-based directions in addition to the address. Include photos of your entrance and any identifying features. If GPS commonly has issues, warn guests in advance.

5. Door Code and Access (9%)

How do I get in? Where is the lockbox? What is the door code? Will you meet us? These questions spike dramatically in the 24 hours before check-in.

The Solution: Send check-in instructions with access codes 24 hours before arrival. Include photos showing exactly where the keypad or lockbox is located. If you use smart locks, explain how they work.

6. Local Recommendations (7%)

"What restaurants do you recommend?" "Is there a grocery store nearby?" "What should we do while we are there?" Guests trust local knowledge over generic travel guides.

The Solution: Create a comprehensive recommendations section in your digital guidebook. Categorize by type (restaurants, activities, groceries) and include personal notes about why you love each place.

7. Amenity Questions (6%)

"Is there a washer/dryer?" "Do you have a hair dryer?" "Is the kitchen fully stocked?" Guests want to know what to pack and what to expect.

The Solution: Include a complete amenities list in your guidebook. Be specific. Do not just say "kitchen". List what is actually in it.

8. Check-Out Procedures (5%)

What do I need to do before I leave? Where do I put the keys? Do I need to strip the beds? Interestingly, many guests ask about check-out before they even check in.

The Solution: Keep check-out tasks simple and communicate them clearly upfront. Guests appreciate knowing expectations from the start.

9. Pet and Child Questions (4%)

"Is the yard fenced?" "Is the pool gated?" "Are there any hazards for children?" Parents and pet owners want safety assurance.

The Solution: If your property is family or pet friendly, highlight safety features prominently. If there are hazards, disclose them clearly.

10. Contact Information (3%)

"How can I reach you if there is a problem?" "Do you have a local contact?" Guests want reassurance that help is available if needed.

The Solution: Provide multiple contact methods and set expectations about response times. Include emergency contacts for urgent issues.

The 87% Solution: Automating Guest Communication

Here is the most important insight from this analysis: 87% of these questions have answers that do not change from guest to guest. Your WiFi password is the same. Your parking instructions are the same. Your local recommendations are the same.

This means you can answer the vast majority of guest questions before they even ask them—automatically—with a comprehensive digital guidebook.

The remaining 13%? Those are the questions that actually require your personal attention. This includes special requests, unique circumstances, or genuine issues that need human judgment.

How I Reduced Guest Messages by 80%

After this analysis, I restructured my entire guest communication system. Here is what changed:

1. Created a comprehensive digital guidebook that answers every question from my top 10 list. Every. Single. One.

2. Added AI Chat to my guidebook so guests can ask questions in natural language and get immediate answers, even at 2am when I am asleep.

3. Sent the guidebook link earlier. Now it goes out with the booking confirmation, not just before check-in.

4. Used QR codes in the property that link directly to relevant guidebook sections.

The result? My pre-check-in messages dropped by roughly 80%. The messages I do receive now are almost exclusively the 13% that actually need my personal attention. Special requests, genuine concerns, or just friendly hellos.

The Time Savings Add Up

Let me do some quick math. Before optimizing:

• Average of 8-10 messages per booking
• ~3-5 minutes to read and respond to each
• 30-50 minutes of messaging per booking

After optimizing:

• Average of 2-3 messages per booking
• Same 3-5 minutes each (but for meaningful conversations)
• 10-15 minutes of messaging per booking

At 100 bookings per year, that is roughly 25-35 hours saved annually. That is just on pre-check-in communication. That is almost a full work week reclaimed.

Build Your Own Question-Answering Machine

You do not need to analyze 500 messages to benefit from this insight. Start by:

1. Track your messages for one month. Note every question guests ask. You will quickly see patterns emerge.

2. Create a digital guidebook that proactively answers your top questions. Make sure it is mobile-friendly and easy to navigate.

3. Send it early and often. Include the link in your booking confirmation, pre-arrival message, and check-in instructions.

4. Add AI Chat capability. Let guests ask questions in their own words and get instant answers from your guidebook content.

Stay Pilot makes this entire process simple. You can create a comprehensive digital guidebook in minutes, and our AI Chat feature turns your guidebook into an always-available assistant that answers guest questions 24/7.

The best part? You are not removing the personal touch. You are freeing yourself up to provide it where it actually matters.