Fewer short-term rentals in Chester could indicate a softening market

By Shawn Cunningham
© 2025 Telegraph Publishing LLC

At last week’s Chester Select Board meeting, Zoning Administrator Preston Bristow and Assistant ZA Hugh Quinn updated the board on the town’s short-term rental program, which seems to have cooled down along with the entire STR market in general.

The town requires property owners who rent for short periods of time — including through online platforms like AirBnb and VRBO — to register with the town and provide some information about their property and how it’s rented. Unhosted rentals are also charged $600 per year and those with a host on site are charged $150 per year.

Last year, the board instituted a cap on the number of short-term rentals as well as a one-year waiting period for new short-term rentals including those where a building has been an STR but has changed hands. The cap was set at 65 but at the time there was a total of 70.

According to Quinn, there are currently 64 registered although a handful have not renewed and have been given a grace period. There’s also a waiting list of four rentals, one of which is not eligible due to the one-year waiting period.

Quinn also noted that several of the properties, including those that have had their registration renewed for 2025, are for sale. Those that do sell will not be eligible to become STRs for one year and if the number of STRs registered then is at 65, those properties would have to join the waiting list.

Quinn said the ratio of hosted to unhosted was 19 to 45.

Grace period lapses, number of STRs drops

Since the March 5 meeting, the grace period that Chester’s zoning office had given for STR renewals due in January has lapsed and several property owners have not renewed. That includes two hosted rentals and one unhosted, reducing the total number of rentals to 60: 17 hosted and 43 unhosted.

None of the three owners on the wait list has applied and paid the fee for registration and while there are a handful of people who have inquired about registering, none of those has asked to be placed on the waiting list, according to Quinn.

Of those properties that are either registered or have been registered in the past, at least 10 have sold or are for sale today. In fact, if all of those that are for sale now were to be sold, the list would drop into the low 50s and it doesn’t seem like there will be a rush to fill those slots.

Quinn says that every couple of months, someone inquires about buying a house and renting it short-term. He said that he mentions the one-year waiting period, which may deter potential landlords.

Market cools, but will that open up housing?

With companies like AirBnb and VRBO working to increase their portfolios of rental properties, there has been talk about the decline of rental days per property for the past couple of years. But the short-term rental data firm AirDNA sees other factors that may shrinking the market.

“High interest rates, rising home values, and declining growth in short-term rental performance have made it tougher to invest in short-term rental properties over the past few years. These challenges are expected to persist into 2025…” writes AirDNA on its website.

While the decline in rental days per property may be prompting owners to sell, it may not boost affordable housing locally any time soon. That’s because property owners who bought relatively inexpensive houses in the Covid-19 years are often looking to make a killing on turning those houses.

In Chester, for example, comparing a home’s purchase price according to the grand list with the active real estate list price shows desired profits in upward of 300 percent.

• A house purchased in April 2021 for $180,000 is now listed for $699,000. It’s been on the market for 296 days.
• A house purchased in August 2021 for $110,000 is listed today for $509,000. It’s been on the market for  88 days.
• A house bought in June 2022 for $147,500 was first listed for $479,000 but is now listed for $319,000, after 307 days on the market.

Some owners upgraded their homes to make them more attractive to renters, and that lowers any profit. But taking into account such upgrades, even a “mere” 100 percent profit would keep some of these homes affordable for local residents. And if recent predictions of an economic downturn come to pass and even if the prices of these properties drop further, those in need of affordable housing may be the least well-positioned to take advantage of them.