07-05-2025
Peek inside the most wish-listed Airbnb in Massachusetts: the ‘Gingerbread House' in the Berkshires
Located in the town of Tyringham (population 427), the Gingerbread House is part of
Kitson 'began transforming the property around 1920, turning the existing dairy barn into his art studio and called it Santarella,' the
'Affectionately known as the 'Gingerbread House,' the most striking feature of his studio is its 80-ton, asphalt-shingled storybook roof. He created a cluster of other fairytale-inspired buildings, including a cottage and detached tower, which he used as additional studio space. These projects, along with an enchanting garden with exotic plants and fish, would become Kitson's primary focus for the last 25 years of his life,' it says.
According to Massachusetts Historical Commission records, Kitson's artistic vision for his property was not always appreciated by locals, some of whom 'called him a 'bit titched in the head,' for to them his home and studio, inside and out, even his few acres, were plain crazy.'
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The Gingerbread House Tower was named the most wish-listed Airbnb listing in Massachusetts.
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But to Airbnb guests, the property can provide a magical escape from day-to-day life.
There are four units on the Santarella estate. The owners live in one unit, and the other three are available as
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The
It's situated on nearly four acres that includes 'lovely gardens, beautiful lily pond, stone bridges, a running brook, stone bench seating area with 'chiminea', and wooded area,' the Airbnb listing states. Visitors can also explore nearby walking trails.
'The open concept living space filled with plants brings the outdoors inside and offers ample room to relax,' the listing states.
One of the bedrooms in the Gingerbread House Tower.
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There's a sitting area with a sofa and hanging chair where guests can watch TV or enjoy views of the gardens outside.
'To the right, a bohemian bedchamber with full-sized bed is hidden behind a sliding door,' the listing states. 'Up one step, the 'Tower' section has a suitable kitchenette with microwave, fridge, Ninja Foodi XL, induction cooktop, and a Chemex coffee maker. There is also a cozy eating area with table and chairs. A large bath contains a double vanity, huge walk-in shower and private water closet. Climb the stairs to a loft bedchamber that sleeps two in a queen-sized canopy bed.'
The Gingerbread House Tower was named the most wish-listed Airbnb listing in Massachusetts.
Airbnb Community
Santarella's owners, Joshua Williams and Shaun Mosley, purchased the property in October 2020.
Williams was visiting a friend in the Berkshires when first discovered Santarella in the summer of 2020.
As soon as he saw the Gingerbread House, 'I immediately fell in love,' Williams said in a phone interview. 'I told my partner Shaun, and he fell in love with it also.'
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Joshua Williams and Shaun Mosley own the property known as Santarella.
Joshua Williams and Shaun Mosley
Williams said the income they receive from the rentals is used for maintenance and repairs. One of the latest projects has been fixing the
'One third of the roof is done, the front portion facing the road,' he said.
They would like to finish the rest of the roof 'in the next year,' he said.
Williams said living at Santarella has been 'amazing' and they enjoy having guests experience what they get to see every day.
'We get a lot of visitors,' he said. 'A lot of people driving past and stop very quickly because they're surprised by what they just saw.'
Williams said Santarella can provide an escape from reality, something akin to a getaway to a health and wellness retreat, and they're working hard to keep up the structures and surroundings so they can continue to be enjoyed in the years to come.
'It's just so wonderful,' he said, and we're 'glad our passion and hard work is benefitting others.'
Emily Sweeney can be reached at
