HB Exclusive: 388 Ventures acquires Callicoon Hills

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 in the Western Catskills.

The company 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 a restaurant, bar and coffee shop, a barn for large-scale events, a 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 close to both Callicoon and Livingston Manor, two towns that have become popular destinations known for their 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 a track record of breathing new life into historic assets.

“For many years the Catskills was seen as a lower-key escape from city life relative to more established destinations such as the Hamptons and Hudson Valley,” Seth Johnson, partner, 388 Ventures told Hotel Business. “These days, the region emerged with its own unique gravity and draw thanks to its unmatched access to nature, flourishing food scene and close proximity to New York and Philadelphia. We are honored to be a part of this next chapter of Callicoon Hills and offer an authentic Catskills resort experience to visitors from near and far.”

Life House will serve as 388’s full-service management partner, overseeing hotel, restaurant and event operations. The company, which has raised nearly $100 million 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 U.S., Mexico and Canada. As a third-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.

“We are humbled by the opportunity to grow our partnership with 388 Ventures through the off-market acquisition of Callicoon Hills, our first hotel in the Catskills and largest dedicated events operation yet,” Bryan Dunn, managing director/head of growth, Life House told Hotel Business. “The property’s impressive campus and its expansive amenity base makes it an amazing destination not only for year-round getaways, but also for weddings and corporate retreats which are in extremely high demand in the region today.”

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.