What's the Best Way to Coordinate Our Family Cabin?
A reader asks how to move beyond group texts and scattered emails when managing a shared family property.
The Question
"Our family has owned a cabin in the mountains for three generations. There are now five families who share it—my siblings, cousins, and I. We're constantly texting back and forth about who has which weekend, when the property tax is due, whether someone can check on the place after a storm, and a million other details."
"The group text has gotten completely out of hand. Last month, two families showed up on the same weekend because of a miscommunication. We've lost track of who was supposed to arrange the annual septic inspection. And nobody can ever find the WiFi password when they arrive."
"What's the best way to coordinate all of this? We need something that works for everyone, from my tech-savvy nephew to my parents who can barely use email. Help!"
The Answer
It sounds like you have a wonderful family cabin with a rich history. The fact that it's stayed in the family for three generations speaks to how much everyone values it. But you're right—coordinating five families without a proper system is a recipe for frustration, and eventually, family tension.
The good news is that you have options, ranging from simple free tools to comprehensive platforms designed specifically for situations like yours. Let's look at what might work best, starting with the simplest approaches and working up to more robust solutions.
Option 1: A Shared Digital Calendar (Free, But Basic)
What it is: Google Calendar, Apple Calendar, or Outlook Calendar with sharing enabled so all five families can see the same calendar.
How it works: One person creates a calendar called "Family Cabin" and invites everyone else. Each family adds their stays as calendar events. Everyone can see who has booked which dates.
What this solves:
- •Everyone sees who has the cabin when
- •Reduces double-booking confusion
- •Free and familiar to most people
- •Works on phones, tablets, and computers
What it doesn't solve:
- •Anyone can accidentally edit or delete someone else's booking
- •No way to track if usage is fair among families
- •Still need group texts for everything else (WiFi password, maintenance, bills)
- •No approval process for high-demand weekends
- •Nothing to help with maintenance coordination
Best for: Very small groups (2-3 families) who trust each other completely and don't have complex needs.
Option 2: Shared Calendar + Cloud Folder (Still Free, More Complete)
What it is: A shared calendar for bookings combined with a Google Drive, Dropbox, or iCloud folder for storing documents.
How it works: You use Option 1 for scheduling, but also create a shared folder where you store a document with the WiFi password, house rules, vendor contact information, maintenance schedules, and property expenses.
What this adds:
- •Everyone can find important information in one place
- •No more searching through old texts for the plumber's number
- •You can share photos of the circuit breaker locations or how to work the tricky fireplace
- •Still free
The downsides:
- •Now you're juggling two different systems
- •People forget to check the folder and still text questions
- •Documents can get messy (10 different versions of "Cabin Info.docx")
- •Still no approval workflow or fairness tracking
- •No notifications when something changes
Best for: Small groups willing to be very disciplined about updating documents and checking the shared folder regularly.
Option 3: The DIY Spreadsheet Approach (For the Organized)
What it is: A Google Sheets or Excel spreadsheet that combines calendar, contact list, expense tracker, and maintenance log all in one file.
How it works: Someone creates a comprehensive spreadsheet with tabs for the calendar, contact information, expenses, maintenance tasks, and house rules. Share it with everyone and pin it in the group text.
Why some people love this:
- •Everything in one place
- •Customizable to your exact needs
- •Can add formulas to track expense splits or usage patterns
- •Free
The reality:
- •Requires someone to build and maintain it (that person will get tired)
- •Not mobile-friendly—hard to use on phones
- •Less tech-savvy family members will find it confusing
- •Someone will accidentally delete a row or mess up a formula
- •No automatic notifications when things change
Best for: Tech-savvy groups with one very organized person willing to build and maintain the system.
Option 4: A Platform Built for Shared Properties (The Complete Solution)
What it is: A platform like OurSharedPlace that's designed specifically for families and groups who co-own vacation properties.
How it works: Instead of piecing together multiple tools, you have one platform that handles bookings, documents, contacts, maintenance tasks, expense tracking, and communication all in one place.
What a purpose-built solution offers:
- •Booking calendar with approval workflow for high-demand dates
- •Usage tracking so you can see if each family is getting fair access
- •Contact directory for vendors, emergency contacts, and local services
- •Shared blog posts where you can document house rules, WiFi password, how-to guides, and family history
- •To-do lists for maintenance with assignments and due dates
- •Photo gallery to show where things are located
- •Email notifications when bookings are made, tasks are due, or documents are added
- •Guest access for extended family or renters with limited permissions
- •Mobile-friendly so it works just as well on phones as computers
The tradeoff:
- •Everyone needs to sign up and learn a new platform
- •There's a cost (though usually modest compared to property maintenance expenses)
Best for: Groups of three or more families who want everything in one place, with proper permissions, notifications, and fairness tracking built in.
So What Should You Do?
Given that you have five families, a history of double-bookings, and scattered information, I'd recommend starting with either Option 2 (calendar plus folder) or jumping straight to Option 4 (a dedicated platform).
Here's why: With five families, you're past the point where informal systems work. You need proper permissions (so people can't accidentally mess up each other's bookings), notifications (so everyone stays informed), and a single place for all the information (WiFi passwords, maintenance records, vendor contacts, house rules).
If budget is a concern and everyone is willing to be disciplined, try Option 2 for a few months. But be honest with yourself: if people aren't checking the shared folder now, they probably won't start.
For a three-generation property with five families, a dedicated platform like OurSharedPlace will save you so much time and prevent so many conflicts that the cost pays for itself in reduced family tension alone. You can set it up once, and it just works—no one person has to be the spreadsheet keeper or folder organizer.
Getting Everyone on Board
Whatever system you choose, here's how to get all five families actually using it:
1. Have a family meeting (or Zoom call)
Explain that the current system isn't working and present the solution. Get buy-in from everyone before implementing anything.
2. Designate an administrator
One person (or two) should be the point person for setup and troubleshooting. This doesn't have to be permanent, but clarity helps.
3. Transfer existing bookings immediately
Whatever system you implement, add all current reservations right away so nothing gets lost in the transition.
4. Set clear rules
Decide how far in advance people can book, what happens with popular weekends (approval process? rotation?), and what's fair usage.
5. Do a walkthrough for everyone
A quick 15-minute video call showing how to book dates, find information, and use the system prevents months of confusion.
6. Make it the official source
When someone texts "Can I have the cabin May 15-18?" respond with "Please submit that in the system and I'll approve it." Redirect consistently until everyone gets the message.
The Bottom Line
Your cabin has been in the family for three generations because people love it and take care of it. That's special. Don't let coordination chaos damage those relationships or make people dread the logistics of using a place they love.
The right system—whether it's a shared calendar and folder or a comprehensive platform—will give you back the joy of cabin ownership. No more double bookings. No more hunting for information in old texts. No more wondering if usage is fair. Just clear processes that let everyone focus on enjoying the mountains together.
With five families and three generations, you've reached the point where investing in a proper system isn't optional—it's how you protect this family asset for the next three generations.