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Pricing and marketing for the 2020 rental season

Written by Elizabeth Weedon
Pricing and marketing for the 2020 rental season
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Pricing for 2020

Every year at this time, homeowners ask our advice about whether they should go up in their pricing or stay the same. Keep in mind that all those vacationers who signed leases prior to January 1st or started their vacations prior to July 1 were exempt this year. So the lodging tax could have an even bigger impact on vacationers next year than this.   Thus, unless you added a major improvement to your home (like central air conditioning), we strongly advise that you not increase your rates.

Some general tips

Tier your pricing in order to reflect the relative demand from vacationers.
Keep in mind that the “sweet spot” of the summer season is the first 2 weeks in August, the next tier consists of the last 2 weeks of July and the third week of August, the first two weeks in July are next, and the least popular week is the last one in August.  Don’t wait until the last minute to reduce your pricing for those difficult-to-book weeks.

Get early commitments from your past guests.
Even earlier than most of you do.  Knowing they have a first right of refusal, your guests are under no obligation to commit now and would prefer to delay sending you a deposit.  But doing so enables them to change their minds, resulting in your possibly missing out on other inquiries/bookings.  And provide greater incentive to commit early by only offering your “repeat guest discount” if they commit by a certain date. They should be grateful that you are reserving “their week(s)” for them.

Set up a free Owner Special to persuade vacationers to book early.
With the Owner Special link in your Homeowner Center, use the 100 characters of open text to incentivize vacationers: offer a special discount or a gift certificate if they book your home by a certain date.

Get your listing ready for next season now!

We have noticed a significant increase in early inquiries and bookings the past couple of years. This summer, inquiries for next year were up 32% from last year! And last year, inquiries during the fall were 9% higher than the previous year at that time.

Don’t miss the wave!

Make sure:

  • your pricing and availability have been entered for 2020.
  • your pictures are the best they can be (large, clear, well-lit, seasonal).
  • any improvements you’ve either made, or are planning to be ready for next season, are entered on your listing.
  • you keep your calendar’s date stamp as current as possible (at least every few weeks in the off season).
  • you consider adding a free Owner Special to provide incentive for them to book by a certain date or to highlight a special offer of some kind.

To those of you who haven’t yet registered your rental homes with the MA DOR (Dept. of Revenue)  and submitted your first payment, what are you waiting for?  Most of the bugs in the registration and payment process have been worked out by the DOR, and their phone Help Line is very helpful. And remember, you only need to remit a tax for the months in which you charged a tax from your guests. Then you can relax until next season!

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 have managed my family's rental home there since the mid-1980’s. I’m passionately devoted to the Vineyard – and to, which I credit with enabling me to hold onto the special property that has been in our family since the 1920’s. An enthusiastic member of the Homeowner Support Team, I am particularly involved with our new listers, providing assistance with the sign-up process and advice about how to create the most effective listing to ensure their booking success with us. I have recently taken over our press and public relations needs. And, with owner Joan Talmadge, I am also responsible for editing and writing much of the content on our website, our monthly newsletters, and the blog posts. My husband and I live in Wellesley where we have raised our 2 grown kids and our Black Lab, Maisie. Email Elizabeth


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