Op-Ed: Short Term Rentals—Boon or Bummer?

Although adding to the overall supply of permanent housing at all price points is a more important goal, Kent County also needs additional rentals for tourists and short-term visitors. In Chestertown, this demand tends to be cyclical, with peaks for college graduation, the wedding and hunting seasons, and major town festivals. The 2026 Town of Chestertown Comprehensive Plan suggests ways we might increase both short and long-term rental housing in our existing single-family neighborhoods. Whether rented to tourists or local residents, adding legal accessory dwelling units to homes in single-family neighborhoods will make good economic sense for many of us.

As in other destination communities, some Chestertown property owners already offer rooms or even whole houses as short-term-rentals (STRs). These property owners and most downtown businesses welcome the extra income generated by the visitors.  Many of their neighbors, on the other hand, complain of noise, trash, parking problems and a loss of neighborliness. STRs may also drive up housing costs for local residents by reducing the number of longer-term rentals. These vacation rentals do generate revenue for the Town through an existing hotel tax. In FY 2026, Chestertown earned more than $225,000, although most of this income was from our three motels and a few larger inns and B&Bs.

The Chestertown Town Council recognizes that its charter and ordinances were written before vacation rentals became so popular.  Considering this issue in the context of our overall housing goals might be beneficial as the Town updates its zoning ordinances. We also must consider the legal implications of regulating economic activity. At present, there are about forty STRs in Chestertown and another 175 in other parts of Kent County. We should anticipate increased demand and implement clear and sensible guidelines.

The new Comprehensive Plan proposes zoning that allows and encourages greater density in single family neighborhoods. According to data in the Plan, the need is acute. Currently, fewer than a quarter of all rental properties are under $1000 per month.  More than half of our subsidized housing units will lose affordability restrictions by 2030.  75% of Chestertown households consist of only one or two persons. The number of studio and 1-BR rental units has dropped by 40% since 2019.  Obviously, there is not a good fit between supply and demand, especially for those on limited budgets.

So, how can Chestertown best welcome tourists, add affordable rental units AND give homeowners some needed extra income?  What if all possible extra housing is just converted to vacation STRs? How can we  instead increase much-needed affordable rental housing? After comparing the practices in many other destination locations, I believe the “home-sharing” model for short-term rentals is best suited to preserve our unique community character.

In general, this “sharing” or “hosting” system prevents absentee owners from operating full-time vacation rentals by requiring all STR properties to be the owner’s legal primary residence.The sharing model generally requires the homeowner to remain on-site as host during the guests’ stay for any rental less than 30 days. Each community can of course tweak parking, minimum stay, maximum number of guests, and other details.  Both Santa Monica, California, and Charlottesville, Virginia, have adopted variations of this basic system.

In Chestertown, for instance, a homeowner might offer a “granny flat,” garage apartment, accessory dwelling unit (ADU), or even the main house to short term visitors. For some properties, the income would more than cover the extra cleaning costs and the hotel tax. These owners also might enjoy introducing our town to visitors. For them, operating a STR could be an economic and social boon.

Most homeowners, however, would find both the extra work and the loss of privacy a real bummer. For them, renting out their new apartment or ADU on a longer term lease would make much better sense. Instead of meeting weekly strangers, they would be sharing their property with a real neighbor and earning some useful extra income.

There are no absolutely right or wrong ways to manage ADUs and STRs. Only a healthy and open dialogue will ensure the compromises needed.  For more background, I found “How Should Airbnb Be Regulated? on govfacts.org to be a useful source.  The Chestertown Town Council expects to start discussion of a revised STR Ordinance this year. Council members would welcome input from residents.

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Sheila Austrian represents Ward 1 on the Chestertown Town Council. Her first adult job, at the Bureau of Urban Research at Princeton University, started a lifelong interest in what makes cities work. She recently participated in the KNOCK! Chestertown meetings, sponsored by the Kent County Local Management Board, that discussed housing, education and economic mobility. This paper will be the first of several to suggest ways Chestertown residents can benefit from welcoming new neighbors. The opinions expressed are her own and do not represent official policy.