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The Mast-Head: A Few Thoughts on Airbnbs

Wed, 12/17/2025 - 11:43

While on the road lately, I have generally stopped overnighting at hotels of the Holiday Inn sort and instead tried when possible to book short-term rentals. It has been an education.

On trips off Long Island, mostly to visit the kids away at school, I have stayed in a variety of places, including an unheated onetime chicken coop and a room above a Maryland cafe where the chatty staff arrive about 6:30 in the morning to set up.

I stayed in a geodesic dome in Vermont with cardboard on the floor for insulation. Another night was above a tattoo parlor open late. Some mattresses felt as if they had been rescued from a landfill; others made for a superb sleep. Over all, the rentals are a lot more interesting than the hotels, and often significantly less money.

Here on the East End, the towns attempt to gain some level of control of Airbnb properties by way of rental permits. How many landlords keep up with this is difficult to say. I lost interest quickly after clicking around one of the online listing sites looking for even one permit number, as mandated by the local laws.

From what I have seen, officials do not have the time, or perhaps the motivation, to keep after these things. Town ordinances try to limit the number of stays per year, but they have had negligible effect on reining in the thousands of constantly changing offerings. Worse, the current rules turn a vast segment of the property owners into scofflaws.

Bringing short-term rentals into a new kind of legal framework could boost public dividends through the accommodation taxes collected by the county. Penalties for noncompliance might be strengthened to create an incentive for property owners to comply — at a minimum with safety standards. Beyond that, I have nothing much else to suggest to local officials.

Short-term rentals are here to stay. A new approach focused on curbing party houses and other obvious annoyances might be called for. It seems there is not much more anyone can do, whether we old-timers like it or not. 

 

 

 

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