Castle Peak co-CEO talks everything Trailborn

NEW YORK CITY – Castle Peak Holdings, the investment arm of the outdoor-focused and Marriott-supported Trailborn hospitality brand, has closed its second fund with $315 million committed to accelerate growth of the eight hotel, 690-key platform founded in 2021.

Most recently, the investors acquired the Snow King Resort in Jackson Hole, Wyoming, marking the first deal for the new fund. The 203-room resort will undergo renovations to upgrade and expand the on-site amenities, and enhance the building’s exterior, lobby, meeting spaces and dining offerings. It marks Castle Peak’s largest acquisition and follows the openings of Trailborn Grand Canyon in Williams, Arizona, the Trailborn Surf & Sound in Wrightsville Beach, North Carolina, and the Trailborn Highlands in North Carolina’s Blue Ridge Mountains.

In just over a year, Trailborn has opened five properties and has an additional property debuting in Mendocino, California, within the next year.

Castle Peak Co-Founder and Co-CEO Ben Weinberg told Hotel Investment Today that, along with his partner Mike Weiss, the investment firm expects to deploy the fund over the next 24 to 36 months and acquire between five and 10 assets – likely closer to five – with the next deal likely to come in the third or fourth quarter.

The first acquisition from Castle Peak's new fund was the Snow King Resort in Jackson Hole, Wyoming.

Weinberg said Castle Peak and Trailborn are staying true to their mission of converting assets in iconic outdoor destinations that include national park gateways, beach towns, lake towns, ski and wine country destinations where it’s difficult to build hotels and where people can’t find a strong 4-star lifestyle product.

Moving forward, Weinberg said they will be a little less focused on 63-key hotels that they bought in the early days and instead buy 100- to 200-key hotels – but in the exact same markets with the exact same products and repositionings.

Sourcing deals remains challenging, Weinberg added, which is why they have a team that works hard to find off-market deals and why they tend to imbed into markets to get to know the players and opportunities.

“We have 35 people here in our offices and one of the first hires that we made was a business development person to source and originate deals, helping us focus on off-market transactions, which has been the entirety of our focus since inception,” Weinberg said. “We really lean into building an off-market sourcing function and getting to know these communities in these destination resort markets.”

But he was quick to add that the right deals can take years to come together, citing one deal conversation with one potential seller that started five years ago. “Those types of owners are maybe now a bit more open to selling potentially than they were five years ago,” he continued. “We’re seeing some sellers willing to engage in discussions that they weren’t necessarily willing to do maybe two or three years ago. But it’s still tough. It’s a tough transaction market, and the bid-ask spread is certainly still there.”

Repositioning challenges

Once they do get deals done, Castle Peak and Trailborn still face uncertainty on FF&E production given the tariff environment.

We’re seeing some sellers willing to engage in discussions that they weren’t necessarily willing to do maybe two or three years ago. But it’s still tough. It’s a tough transaction market, and the bid-ask spread is certainly still there.

Ben Weinberg

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“I would say it’s much, much more nuanced than the headlines,” Weinberg said. “You have manufacturers in China who are willing to eat some of the tariffs just to keep their factories moving and take orders from people like us. You also have U.S. domestic manufacturers that look a little bit more attractive than they did before. And then, of course, you have Vietnam, Malaysia and some from Mexico that are becoming more competitive. So, there was a little bit uncertainty for us as to who to work with, why and what the surrounding factors and impacts of the changing global order as we see it will have on us and our furniture orders. We’re seeing that clear up now, but the tariff environment that we’re living in is not entirely clear.”

Weinberg said that they have to talk to more vendors, understand with more granularity and transparency who they’re working, how they’re positioned and ensure they will live up to all their deliverables.

In addition, he said subcontractors continue to be elusive. “There’s just a lot of time spent negotiating, managing and ensuring that we’re getting the best execution at the best possible price from a group of subcontractors with availability that’s just tighter than it used to be.”

Performance holding up

On the performance side, Weinberg said thankfully they have not yet seen the choppiness and volatility they’ve been expecting this year.

We expect to see choppiness and volatility in some form. We are not of the view that everything happening in the world will have no impact on our guests and our consumer and their travel. There has to be some level of impact… We’re certainly not as positive as we were six or nine months ago, but we’re not seeing a crash either.

Ben Weinberg

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“We expect to see choppiness and volatility in some form. We are not of the view that everything happening in the world will have no impact on our guests and our consumer and their travel. There has to be some level of impact… We’re certainly not as positive as we were six or nine months ago, but we’re not seeing a crash either.”

Weinberg said top line revenue remains stable with labor costs, especially, impacting the bottom line for a somewhat seasonal resort and destination resort business.

“We’re a little bit more accustomed to those challenges than everyone else is seeing,” Weinberg said. “We’ve seen some level of cost expansion over the course of the last 24 months, but we certainly haven’t seen an acceleration of that over the course of the last six months. If anything, we’ve seen a little bit of a little bit of a loosening in the labor market.”

What has to be helping Castle Peak and Trailborn drive the top line is the new relationship with Marriott International. In 2024, they entered into a long-term agreement to add Trailborn's portfolio to Marriott’s distribution system.

With Trailborn’s inventory having gone live on Marriott’s platform toward the end of 1Q25, Weinberg said it was a bit early to quantify results, but he did say they were optimistic about the relationship’s ability to drive rate and occupancy for different reasons, at different times of the year, especially in more seasonal markets.

In summary, Weinberg stated, “Closing this vehicle is a testament to the durability of our model and the belief that exceptional outcomes come from doing the hard work ourselves—strategically, creatively, and operationally. We’re a team of deep sector specialists, and we believe our relentless, singular focus positions us for success in this type of environment.”