The Coolest Getaway Spot On Airbnb

Between the two of them, Brooke Baxter Bailey and her husband, Jeff Bailey, have founded an underground performance-art space, a live-music venue, a piano bar, and a coffee-and-tacos shop —all in Williamsburg. Their latest venture, however, has taken them Upstate: The couple have opened the Glass Mountain Inn, part Airbnb-style getaway, part event space, in Phoenicia, NY. In other words, the rapidly Brooklyn-ifying Catskills just got a little bit cooler.
“We found this property, a beautiful 1865 farmhouse with three rental units and a barn. We weren’t thinking, Where can we be innkeepers? We thought this could be our home and our business,” Brooke remembers. “We had sold our stakes in New York,” adds Jeff.
The couple met a decade ago at Glasshouse, Brooke’s first entrepreneurial endeavor. When Brooke had moved to Williamsburg a few years earlier, she was scraping by: “I was an assistant to a matchmaker, I was booking live music at the Cutting Room, cleaning some guy’s house, selling T-shirts on the street, writing poetry. I did some nude modeling for painters. Then I met the Freestyle Family, a group of young guys who were really submerged in the art world, but also trying to carve their own path.” Together, they would do artwork in the street or have parties where everyone would get together and put on improv plays.
When Brooke decided she and her friends needed a bigger space, Glasshouse was born. “It was very underground, very DIY, very wild.” Jeff, a touring musician, was part of that energy. He helped book bands at Glasshouse and then, when Brooke moved on to open her next project, Glasslands, a bar and event space in the same building, Jeff built a bedroom in the back and did odd jobs for Brooke and her business partner, Roland Hu. “I was the custodial troll that lived in the back,” Jeff jokes.
When the couple got married in May 2012, Brooke was onto her third project, The Manhattan Inn, a piano bar and restaurant in Greenpoint, and Jeff was the owner of the now-shuttered Whirlybird, a tiny coffee shop and taqueria.
When they had a baby, they decided to leave Williamsburg, sell The Manhattan Inn, and move full-time to the Catskills, where Brooke already had a vacation home. "I had been coming up to the Catskills since I was two, because my father was a stand-up comedian in all the Borscht Belt bars," Brooke says. "We love the area, we love the people, and we love the way we spend time here."
And then, of course, a new business, the Glass Mountain Inn, was born. About their ventures over the years, Jeff says, "Brooke and I never worry that we're going to not know what to do. She's an amazing cultivator of space. I'm very likable, and I can pretty much do any skilled or unskilled labor.”
Brooke sees the inn as an extension of her previous businesses. "What I really enjoy is creating an environment that makes people feel good and makes them feel welcome," she says. And, then, there's the "glass" connection, which comes from a line in a poem Brooke wrote long ago: "I could walk a mile in your glass shoes." Click through for more photos of this paradise on Earth.