A castle-style guest house that was part of Derek Jeter’s Greenwood Lake compound is now available on Airbnb for a little over $1,300 a night, according to the listing. The one-bedroom, two-guest rental occupies the historic Tiedemann Castle guest house on a four-acre lakeside property in New York’s Hudson Valley.
The property hit the short-term rental market last month and is being managed by Upstate Luxe, a luxury rental firm run by founder Lisa Mulcahy. Mulcahy said the listing was designed with the estate’s high-profile past in mind and offers boutique concierge services and optional add-ons such as private yoga classes, in-house catering and local excursions. The listing requires a minimum two-night stay.
Tiedemann Castle was built in the early 1900s by a New York physician, at a time when Greenwood Lake was a fashionable summer destination for New York City elites. The guest house retains a stony facade, medieval-style turrets and battlements intended to evoke a German castle. Mulcahy said guests can access part of the guest house’s turret, which contains a yoga space and a sauna at its base, and a private porch overlooks the lake.
The rental includes direct access to the property’s private dock and about 700 feet of lakeside frontage. The broader compound, which Jeter owned in the early 2000s, includes a 9,000-square-foot main house, a pool house, a boathouse, a replica of the Statue of Liberty and multiple indoor amenities such as four kitchens, a media room, an elevator and a gym.
The property’s ties to Jeter extend beyond recent ownership. The estate was acquired in 1952 by John and Julia Tiedemann, the adoptive parents of the ballplayer’s grandfather, William Connors. The property had fallen into disrepair by the time Jeter purchased it in the early 2000s; reports say the former New York Yankees captain invested about $3 million in renovations to restore the compound.
Jeter listed the property for sale in 2018 for $14.75 million, four years after retiring from the Yankees. The road to a sale proved protracted: the estate went through several price reductions and an unsuccessful auction before being relisted at roughly $6.3 million in the summer of 2024. It went into contract quickly and closed at about $5.1 million later that year. The guest house is now offered separately on the short-term market by the current owners, who Mulcahy said use the property as an occasional vacation home.
Photographs accompanying the Airbnb listing show interiors that blend antiques with contemporary fixtures: a large stone hearth frames a wood-paneled living room, and many rooms preserve the turn-of-the-century character while incorporating modern conveniences. The listing indicates the owners may place the main house on the rental market at a later date.
Mulcahy said the owners want others to experience the property’s combination of historic character and lakefront amenities. The guest house’s arrival on Airbnb adds to a broader trend of high-end, celebrity-linked properties entering the short-term rental market, where curated stays and bespoke services command premium nightly rates.
The Airbnb listing and property management page list booking details, nightly rates and available add-on services. Interested renters can consult the listing for updated availability and any future expansion of rental offerings on the compound.