388 Ventures Acquires Callicoon Hills in the Catskills, Expanding Partnership with Life House

CALLICOON CENTER, N.Y.–(BUSINESS WIRE)–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.

About 388 Ventures

388 Ventures is a real estate investment firm focused on regional leisure destinations across the United States, with an emphasis on hospitality assets with differentiated market positioning. 388 Ventures invests primarily in lifestyle boutique product in the upper-upscale and luxury segment, with in-house development capabilities to take on transformative renovations. www.388ventures.com.

About Life House

Life House is a vertically integrated hotel software & operations platform focused on increasing profitability and reliability for independent hoteliers. Life House was founded in 2017 as one of the only vertically integrated asset-light hotel companies backed by institutional venture and private equity investors. The company is ambitiously investing in operational systems to make it far more profitable, predictable, and seamless for owners while making the guest experience more reliable for travelers. Today the company has nearly 60 hotels in its portfolio across North America. For more information visit www.life-house.com.


Charlotte Myerberg