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July 9, 2025

Chestertown Spy

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1 Homepage Slider Archives

Short-Term Rentals a Long Term Problem: A Chat With Town Manager Larry DiRe

June 19, 2024 by James Dissette

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For over two decades, the $64 billion short-term rental models like AirBB and Vrbo have roiled the US housing markets, causing a host of collateral concerns aside from those who profit from it, not the least of which is its impact on a community, no matter the size.

In Washington, D.C., for instance, commercial hosts occupy housing resources that could have housed long-term renters in the city.

Historically, STRs have exacerbated housing shortages by making housing less affordable for long-term residents, driving up property values and rents, and reducing the number of units available.

While this nationwide issue is fraught with regulatory and constitutional property rights challenges battled mainly in urban areas, Chestertown and Kent County are not exempt. Rural areas offering scenic getaways have seen the rise in STR popularity, partly ignited by the pandemic and people’s need to “get away” from urban centers.

Chestertown, and wider Kent County, are beginning to face many of the same issues as the trend develops. Currently the county is in the process of identifying unregistered SRTs who are not paying hospitality tax. The county is also installing a new software program to help with tax accounting.

All of these are overarching themes with short-term rentals.

DiRe says that so far, residents, neighbors, and rental owners concerned with short-term rental issues have come to the table with a sense of commonality rather than division.

However, potentially contentious issues like safety inspections and property points of contact must be addressed. A property in Chestertown operating as a short-term rental by an LLC in California compounds the issue of responsibility.

“Right now, we don’t do any of that. We don’t require an inspection, we don’t require a licensing. All we do is want to make sure that they’re paying their taxes. And that’s bare minimal. But there are vacation places all over the country wrestling with this much more fiercely than we are right now,” DiRe says.

The Spy recently talked with Town Manager Larry DiRe about civic engagement when challenges like property rights arise.

According to DiRe, a working plan to address short-term rentals could be many vacation seasons away.

This video is approximately eight minutes in length and is part of a discussion to be published next week.

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

Filed Under: 1 Homepage Slider, Archives

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Letters to Editor

  1. Jamie says

    June 19, 2024 at 8:35 AM

    Thank you Larry.

  2. Nancy McGuire says

    June 19, 2024 at 3:31 PM

    Thank you, Larry, for speaking out about this unfortunate issue. There are also safety issues – no requirements for fire prevention. Plus the intrusion in to privacy/peace of neighbors. No one knows who or how many are are renting. VRBO and AirBB never meets the tenants. Neighbors must deal with whom they get.

    As you described – a Town becomes a place where “no one cares” for owners live quietly somewhere else.

    Our residents come here because we are not like everywhere else. It is important that we try our best to protect those values. Why “foul our own nest”, as they say. We can be progressive while remembering this great place has grown and been protected over 300 years. Why have one generation spoil a treasure.

  3. K johnson says

    June 21, 2024 at 3:33 AM

    Vacation Rentals are businesses. Why are they permitted to operate in residentially zoned areas.
    In my opinion it should be illegal to advertise and rent without the permission on the residential neighbors. People who live in residential areas (maybe the actually interpretation of residential needs to be clearly defined) deserve to enjoy a certain sense of familiarity w their neighbors.

    This might work:
    1. Town decides how many vacation rentals are
    acceptable
    Establish and maintain that number..
    What is the least amount of time (days) permitted
    On Longboat key in Florida it’s a month and can only be rented 2x per year. But that a different location type.

    2. If property is in a true residential zone then it requires a permit for variance. It is a business and non compliant. That permit could include lots of questions (number of people/cars/noise/etc)

    Permit application has to be provided to the nearby residents for approval. This is an annual permit costing $500 or more a year. This at least makes the property owner take responsibility for their renters actions..since residents get the permit every year and can yea or nay based on prior incidents (important)!

    3. All signs are by the town. Any other signs are illegal. The towns design in keeping with flavor of the town. They have permit numbers on them. Sign has a cost.
    Each property gets a new sign (turning in the old sign to get a new one) when the approval is granted.

    Business license is required.
    Lodging taxes need to be paid.
    Sales tax too.

    The town can control this. Realtors need to advise buyers of the new law. Steep fines should be imposed for anyone renting without a permit application approval.

    These are just my ideas but I’ve seen this issue in Europe and seen how they try to enforce it …it’s too out of control! Generational families no longer know who they live next to..because they don’t. No one lives there! It’s a business in a residential area.

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