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Updated over 3 years ago,

User Stats

10
Posts
5
Votes
Will Walker
  • Norwood, MA
5
Votes |
10
Posts

Short Term Rental Tax MA - Guidance/Questions

Will Walker
  • Norwood, MA
Posted

Hello Everyone!

My family has owned a rental home on the Cape for as long as I can remember, and the past few years I have taken more of a leadership role in managing the property.

With that said, I am looking for some guidance in making sure I help my family file the tax correctly online.  We have created an account on MassTaxConnect already as it is required to do so. (Filed as an Operator.)

The first renters come in July 2nd all the way up through September 6th (Labor Day).  Different renters come in weekly (as change over is either Friday or Saturday), no renter exceeds being down there for more than 14 days per stay, so there is never a complication of it being a long term renter.

My family did not have to file last year as we did not have renters due to the pandemic, so this is our first year going through this process.

We are not going through an agency, so we have to do the filing on our own.  We incorporated the tax with the payment and have documentation of weekly rates including fees + tax (the Cape is not cheap!).

Because this is our first time filing this Short Term Rental Tax, I am looking for reassurance that we are doing this correctly and if anyone has any experience doing this I would love to hear your story! (It is understood that for tax/legal advice I should always speak with a tax/legal professional, so whatever you feel comfortable sharing is much appreciated.)

Is it difficult to send in the tax? 

Should I file it a month early if the rent checks are coming in a few weeks prior to guests actually vacationing at my rental home?

Anything else you think I might be missing?

Am I overthinking this?

Thank you all for the time and I look forward hearing from you!

-Bill Walker