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July 30, 2025

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The Rental Crisis : A Chat With Town Council Member Tim O’Brien

February 26, 2024 by James Dissette

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If you search Google “house rentals in Chestertown, Maryland,” you might be surprised at the number of advertised properties—only to discover that they are short-term rentals offering no prospect of long-term leases.

With Airbnb at the forefront, this nationwide phenomenon has brought problems to the housing market, not the least of which is the dwindling number of affordable long-term house rentals, the impact on long-term rentals for town residents, workforce housing, and the rising cost of home ownership.

At a county commissioners’ meeting last summer, at least 138 properties on more than 30 rental advertising platforms were identified. They are complex to track and difficult to enforce the 5% lodging tax due to the county and town.

While the County is purchasing a new tracking system to identify short-term rentals, discussions are ongoing about enforcing what has been an honor system of self-reporting tax responsibilities.

The Spy recently talked with Ward 1 Council Member Time O’Brien about the complexities surrounding short-term rentals facilitated by platforms like Airbnb.

O’Brien emphasized the need to distinguish between rentals used for occasional family vacations, licensed bed and breakfasts, and those operating as full-fledged businesses like Airbnb listings.

Ironically, according to old town regulations, existing zoning regulations in Chestertown do not permit short-term rentals in residential areas. Long unenforced, the trend only grew.

“This system of renting out houses on Airbnb or on the web did not exist when the current zoning regulations were put in place. The current regulations do not allow for any Airbnb in residential areas. No short-term rentals are allowed in zones residential one, two, and along the waterfront. If you read our zoning ordinances, it is not allowed, period.”

O’Brien says that when Airbnb began to appear (nationally), it came up against other municipal zoning codes similar to Chestertown’s, and it immediately went to court, where it was determined that Airbnb is a private enterprise, a private exchange between people. The old zoning regulations don’t apply andtrying to enforce them would only incite law suits.

“We now have LLC-owned rentals that are not even registered in Maryland, LLCs owning property in Chestertown for the sole purpose of renting out homes, meaning now there are homes that are businesses rather than residential for families or people. I’m not against private business. But these are residential areas,” O’Brien says.

Currently, the town and county are exploring ways to implement more oversight.

O’Brien offers Millington as an example of how a town can address the short-term rental proliferation and has proposed considering a similar ordinance requiring permits, registration, and on-site presence for Airbnb hosts; restrictions towns can legally impose on rentals.

O’Brien says he wants to see the town council balance the benefits of short-term rentals with community interests.

This video is approximately ten minutes in length.

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

Filed Under: Archives, Spy Highlights

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Letters to Editor

  1. Nancy McGuire says

    February 26, 2024 at 3:37 PM

    AirB&Bs are a tremendous problem! Believe me, I lived next to one that suddenly appeared. They are a commercial enterprise in residential areas that appear with out permission or anyone knowing. They ignore privacy of neighbors; create fire safety issues; noise issues, parking issues and more. I researched ordinances across US. There are thousands. Large metropolitan area, small villages, resorts, etc. These areas learned the hard way. The revenue a town can realize from a 5% tax does not cover the cost to an area. Someone described Cape Charles, for instance, as “A PLACE WHERE NO ONE CARES.” Owners are out of Town and care little or nothing about the town or its residents. They only care about their “cash cows”.

    Anyone can research the locations were there are ordinances controlling, and many cases, banning AirB&Bs. For instance, New York City now has a strong ordinance controlling AirB&B (Sept. 2023. Chestertown can not solve the parking issues until they control AirB&Bs.

    The residents in Chestertown do count!

  2. Sonja Leonard Leonard says

    February 27, 2024 at 7:46 PM

    PAY PEOPLE A LIVING WAGE and they will be able to pay the going market rate!! Stop blaming HOUSE SHARING on Airbnb, VRBO, etc. for everything. Go after the huge greedy corporations that have killed MIDDLE CLASS!!!

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