Managing Your Vacation Rental

Managing Your Bookings with Ease!

Written by Elizabeth Weedon
5/5 - (2 votes)

 Updated February 2023 

Often when we meet with homeowners in a group, we ask how many of them take advantage of our free Booking Management system. And we are always surprised how few do! But, when we ask those who use the feature what they think of it, they say things like,

It’s great! I love it! I don’t know how people manage without it! It’s so easy to use and SO helpful!

I, too, wonder how people manage their bookings without it.

Better yet, we’ve now upgraded it to include so many additional really helpful features! 

Now, in addition to how it enables me to keep track of:

  • guests’ names, dates of their stays, number of their party
  • the ages of their kids (and/or dogs)
  • if they’ve been to the Vineyard (where my home is) before
  • any other information about their party that might enable me to make their stay more enjoyable
  • when to send them a reminder for a payment or the directions to my house

Here are some of the new features we’ve added:

  • Additional fields for tracking fees and taxes
  • Automatic calculation of taxes
  • Ability to define multiple payments using the fixed rental rate or a percentage of it
  • Tracking of check-in and check-out times
  • Customizable fields for tracking your specific needs, either per booking or per property
  • Ability to set default amounts and dates for ease of entry

For more information about our latest upgrades to the Booking Management system, listen to this short video:

Some of the system’s many benefits 

Because it’s online, I always have access to it and my guests’ contact information through my online listing wherever I am. 

I love how I can use the system’s settings to generate weekly reminders of what needs to be sent out from me or received from my guests in the upcoming week, or when a document or payment is overdue. 

In the sample below, on the left, you can see the ability to expand each booking record to view its full details.  And in the upper right, you can see the ability to Expand All or Collapse All – or to Export all your booking information on a spreadsheet!

And I love how it automatically syncs with my listing’s calendar, keeping it up to date and also preventing me from double booking anyone. 

And did I mention that it’s FREE?  

Honestly, it’s such a valuable tool that is so under-utilized.  

How can you get started?

If you don’t take advantage of the Booking Management system already, take a look! Log in to your Homeowner Center, and click on the Booking Management link under the “Guest Tracking” section. You’ll never go back to your old process again! 

Need help? See the Booking Management Help page, including a tutorial video. 


About the author

Elizabeth Weedon

Elizabeth Weedon - Although I’ve worked for since 2008, I’ve been a loyal homeowner on the site since early 1998, just a few months after the website was launched by the Talmadges. I grew up summering on the Vineyard and managed my family's rental home there since the mid-1980’s. I’m passionately devoted to the Vineyard – and to WeNeedaVacation, which I credit with enabling me to hold onto the special property that has been in our family for nearly a century. An enthusiastic member of the WNAV Homeowner Support Team, I endeavor to keep my finger on the pulse of the Cape and Islands vacation rental industry so that I can provide homeowners advice about how to ensure their booking success with us. With owner Joan Talmadge, I am also responsible for editing and writing much of the text on our website, our monthly newsletters, and Homeowner Blog posts.