Financial Matters Lodging Tax Managing Your Vacation Rental

Pricing and marketing for the 2020 rental season

Written by Elizabeth Weedon
4.4/5 - (5 votes)

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 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.


  • Our listing of the 65 Cranberry Lane, West Hyannisport MA property lists, in bold lettering, that there is a 14% lodging tax. We are including this lodging tax in our rental rate, and that is so stated in our listing, but the bold statement that there is a 14% lodging tax could discourage some people from reading the entire listing. We have had only 1 inquiry during the past 2 months and we are very concerned about this 14% lodging tax emphasis in our listing. Please let me know how you intend to change this in our listing. Thank you for your assistance.

    • Hi Kurt, Nearly all homeowners post their rental rates without the tax included, so it puts your listing at a disadvantage when vacationers do a search and indicate a price cap, knowing that they will be paying an additional tax. But if you still want to incorporate the tax in your rate, you could post an Owner Special to highlight this. Then when vacationers did a search, the Owner Special will be highlighted on the search results page. You could post the same message you include in the info above your calendar: “No additional fees. The lodging tax is included in the listed weekly rental fee.” But, again, we do not advocate your including the tax in your rates.

  • Greetings Elizabeth
    I used 2018 and it was a huge success. We did not rent last year but will be using the site in 2020. I had referred my neighbor, Roger, on Chestnut St. Falmouth to the site. Do you have a referral bonus? I know the person that had referred me was eligible at the time.

    • Hi, Patricia, yes, indeed! Per our Refer-a-Friend program, if you have a 6-month subscription you are eligible for a free month of subscription time, and if you have a one-year subscription, you are eligible for 2 free months. As you mentioned, your listing is currently inactive, but just give us a call or email us when you go to renew, and we will award you the appropriate free time. Thank you for referring us to Roger!!!

  • Can you suggest any available concise description of the new tax online, that the link could be added to the seasonal booking letter I send out in the fall. I get the sense from renters sometimes that it is an owner’s tax being passed on to them, and not the guests responsibility. I don’t know how to clarify that it is their responsibility, not mine to pay. Thanks.