This as-told-to essay is based on conversations with Briee Della Rocca, an Airbnb host in Williamstown, Massachusetts, about 40 miles from Albany, New York. She converted her two-car garage into an Airbnb to help afford to live in her preferred town. The conversations have been edited for length and clarity.
My husband and I are both New Yorkers, but we moved up to southern Vermont in 2002 or 2003. Having grown up as a renter my whole life, it was wild to see that you could — at the time, anyway — purchase a house in Bennington, Vermont, for less than $100,000.
We weren’t purchasing when we moved up there, but even the rents were so much more affordable. We were early in our twenties, just out of college, and trying to figure out where we would make a life. And a huge factor in that — and what’s remained consistent throughout our choice of where we place ourselves — is whether or not it makes sense and you can afford to live there.
We had a duplex property in Bennington a year into moving there because it was so cheap. That was literally how we, at 22 years old, afforded a house. One side paid the mortgage, and we lived on the other side for free.
We knew it wasn’t a long-term house, and that it was a necessity for the mortgage.
We eventually bought this great house in Shaftsbury, Vermont, for about $250,000, situated on a hill surrounded by mountain views, and we thought we would live there forever. It was a simple ranch, but gorgeous and we loved it.
However, the public schools were not ideal for our family and kids.
We tried them for a couple of years, and they weren’t good at all. So, we started to enroll our kids in private schools, and we realized we’re big public school advocates. We wanted the kids to have a bigger school experience. So we started to look at places where public school systems were known to be good.
When we were looking for our next place to enroll the kids in public school, we wanted my husband to be able to keep his job in Bennington. It’s a dream job, so it needed to be commutable. We had lived in Williamstown before we had children and absolutely loved it here.
The Williamstown, Massachusetts, real estate market is competitive, but we knew what we wanted
People love living here, and they don’t want to leave — who can blame them? So it’s rare that houses come up, and when they do, it’s a very competitive market.
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We were looking for a place where the kids could go to the schools, but we also wanted to be in the town itself, and walk and have sidewalks and be able to let our kids have unplanned meetups — kids still knock on the door and say, “Can so-and-so come out and play,” here. It’s amazing, and we very much wanted that.
Courtesy of Briee Della Rocca
When this house came up, we were the first people to see it. I think it was eight hours after it came on to market.
It’s right in the center of town, and we were like, “Oh my God, we need this house.”
We looked at 10 or 11 houses, but every single one had to clear a few hurdles for me: One of them being it had to be able to produce some form of income.
The house was outside of our budget, but it had a two-car tandem garage attached to it.
Courtesy of Briee Della Rocca
I literally was up in the attic space, and my realtor came in and I said, “This is where we’ll put the guest suite.”
In our last house, we converted our basement into an office for me as well as a guest suite for our family who visited frequently.
We did host the occasional stay on Airbnb, so I had experience, but I was not really thinking of it as a business.
What I really wanted in our new home was consistent income that could be counted on throughout the year. I didn’t know what that was, but I just knew that it would be consistent.
In its first year, our unit made $35,000
We bought the home for $637,000.
We both knew that long-term, living here wouldn’t be comfortable for us on our salaries alone. It would be very difficult if we didn’t have another idea about how we could use our space to make it more comfortable.
Courtesy of Briee Della Rocca
We took out a $100,000 loan to do the renovation. It was a business investment and a home investment because we knew that it would increase the value of our home.
The loan covered basically everything, soup to nuts: Building, driveway, furnishing, the whole bit.
Obviously, we have to pay the loan, so it’s like a small mortgage. Then anything after that is income.
In 2024, it earned $35,000. That was its first year. This coming year, we will beat those expectations — we’re already ahead.
Courtesy of Briee Della Rocca
I was thinking, “What if I designed this space as this one-unit, deeply personal hospitality experience that wasn’t about scaling it or just making a space someone could stay for the night? It was about intentionally reflecting this love letter to this town and to this community and place that we were so drawn to.
We built something that was small — it’s just under 500 square feet — but every choice I made, from the stone counters, to the radiant floors, to the fence, to when you arrive at the Ritz-Carlton bed, is a part of a story. I want you to come in and feel like you got to live inside of this story of Williamstown in the area and retreat and feel like you’ve not only gotten that experience outside in the town, but when you come back into the space itself.
Courtesy of Briee Della Rocca
Community, especially this community, is so important to us.
I couldn’t be gladder to share this with people. It makes me so glad to be here and welcome people, and I love when our neighbors send guests over and we get to host their families. It just feels like an extension of making this community more comfortable for visitors and for the people that live here year round.
