Peek inside the most wishlisted Airbnb in Massachusetts

The glass house perched on 7 private, wooded acres deep in the Berkshires.

This "Mid-Century Glass Octagon" in the Berkshires is the most wishlisted Airbnb in Massachusetts. Courtesy of Airbnb Community

By Cameron Sperance

April 16, 2026 | 10:41 AM

2 minutes to read

If you’ve ever scrolled Airbnb and found yourself saving a listing out of wanderlust, welcome to the wish list industrial complex.

Airbnb this week named the most wishlisted properties across all 50 states, and the Bay State’s winner might surprise you. Massachusetts’ top honoree isn’t a shingled cottage on the Cape or a waterfront Nantucket mansion. It’s a mid-century octagonal glass house perched on 7 private, wooded acres in Otis, deep in the Berkshires. And it has a quirkier origin story than you’d expect.

The “Mid-Century Glass Octagon” is located in Otis, Massachusetts. *– Courtesy of Airbnb Community*

The main living space has floor-to-ceiling windows overlooking the woods. *– Courtesy of Airbnb Community*

The Mid-Century Glass Octagon was built in the 1970s as a kit house by the owners who had purchased the surrounding land as a private ski hill for their friend group, current owner Katherine Auleta said. It was originally off the grid, heated by a single wood stove, and lit by candelabras hanging from the rafters. By the time Auleta, a former New York fashion photographer, became the third owner, the home had been updated by its previous occupants but had drifted into what she described as “twee” territory — lots of colors, lots of little bird things everywhere.

Auleta stripped the interior back, leaned into the boldness of the octagonal structure, installed a mid-century fireplace gifted by a friend, and lined a shelf with photography books hauled up from her old New York City apartment. The result is a 4.95-star, 463-reviewed juggernaut — one of the most-loved homes on Airbnb, per its listing — that regularly books out at a pace that has guests telling her they’ve been trying to lock in dates for years.

“It’s a special home to me, and I love sharing it with other people,” said Auleta, who now lives on an island off Vancouver and manages the property remotely.

Getting to its lofty, wishlisted perch required some guest-driven compromises. Auleta resisted adding air conditioning (the home’s wraparound slatted windows were designed for natural airflow, she said) but eventually relented.

The octagonal space has an open floor plan. *– Courtesy of Airbnb Community*

The kitchen. – Courtesy of Airbnb Community

“That’s what people were asking for, so I did it,” she said. “Your guests are your best teachers, in a way.”

The hospitable philosophy extends to every touchpoint: linen bedding, organic bath products, and a hospitality instinct she traces back to a $3-a-night bamboo hut she once stayed in near Lombok, Indonesia, where French linens and a ceiling fan made a $3 stay feel like luxury.

The Airbnb sleeps four people, according to the listing. *– Courtesy of Airbnb Community*

Guests typically come from Boston, New York, and around the region — often for a romantic weekend, sometimes to get engaged — and they usually bring their groceries, light the fireplace, and stay put.

“The people that really get into the place are the people that are coming to unplug,” she said.

The backyard. *– Courtesy of Airbnb Community*

The back deck has a fire pit. – Courtesy of Airbnb Community

Other New England honorees on Airbnb’s wish list roundup include a modern treehouse with hot tub and water views in Georgetown, Maine; a converted silo house on a Litchfield Hills estate in Connecticut; a tiny cabin retreat in Woodstock, New Hampshire; a tiny eco-cottage with lake views in Smithfield, Rhode Island; and a treehouse with sauna and stream access in Hardwick, Vermont. Consider these wishlisted homes proof that the folks looking for a Northeast getaway increasingly want something off the beaten path for true R&R.