CALLICOON CENTER, N.Y.–Just as summer begins to heat up, New York-based real estate investment firm 388 Ventures has closed on the acquisition of Callicoon Hills, a boutique resort nestled in the Western Catskills. They have tapped tech-enabled management company Life House to oversee end-to-end operations, representing an expansion of their partnership in the Berkshires, where the duo acquired and repositioned three historic hotels into the newly relaunched Lenox Collection.

Callicoon Hills is a 65-key property across 23 acres that encompasses a main Boarding House with restaurant, bar, and coffee shop, a barn for large-scale events, pool, and two other newly modernized buildings with additional rooms. Over the next year, there are plans to expand accommodations with 10 experiential glamping units, which will be operated on a seasonal basis. The property is surrounded by hiking trails that guests can access by foot, and is located only a short drive to both Callicoon and Livingston Manor, two towns that have become popular destinations known for its restaurants, breweries, and boutiques.

The resort was originally conceived by a locally-prominent family, the Hills, in the 1940s, after taking over a turn-of-the-century boarding house. Inspired by the surrounding landscape, they created a camp-like destination known over the years as Hills Villa, Hills, and Hills Country Inn. Recently, as the region boomed with new lifestyle and luxury hotels, there was an opportunity to reimagine the property’s offering. Catering to today’s modern traveler, while paying homage to its authentic Catskills roots, the resort relaunches as Callicoon Hills following an extensive renovation led by Post Company, a Brooklyn-based interior design firm with an impressive track record of breathing new life into historic assets.

Life House will serve as 388’s full-service management partner, overseeing hotel, restaurant and event operations. The company, which has raised nearly $100M in backing from top real estate and technology investors including JLL Spark, KAYAK, Thayer Ventures, Tiger Global, and Inovia, currently has more than 60 hotels signed or open across the US, Mexico, and Canada. As a 3rd party manager, Life House leverages its proprietary in-house built tech stack to maximize financial performance for its real estate partners, while its staff-facing software empowers its on-property team members to deliver a memorable guest experience.

388 Ventures and Life House are actively seeking opportunities to expand their partnership with additional acquisitions in the Catskills, Berkshires and similar drive-to-leisure markets.

Firas Turkmani and Jordan Brustein of Ackman-Ziff represented the seller in this off-market transaction and procured acquisition financing on behalf of 388 Ventures.