Engaging a Management Company: Insights from the Front Lines

When a resort’s HOA board decides to make the leap to a management company, the process can be both anxiety-provoking and transformative. Whether the impetus is staff turnover, dissatisfaction with a current provider, or the need for more sophisticated technology and rental strategies, choosing the right partner is a decision that is crucial to the resort’s future.

Three resorts—Cold Spring Resort in New Hampshire, Gold Point in Colorado, and Neptune House in Rhode Island—each recently engaged a new management company. Their experiences provide a valuable playbook for other boards considering a similar transition.

Cold Spring Resort: Rental Revenue Soars

At Cold Spring Resort, a 77-unit resort tucked between New Hampshire’s White Mountains and Lakes Region, the decision to engage Vacatia was triggered by the retirement of a long-time general manager who had served for 40 years. Rather than search for another single-site GM, the board opted for professional management services that could bring scalable support, modern systems, and fresh ideas.

To transition the retiring GM, Vacatia brought in a new general manager, Joel Stoyer, who was already familiar with Vacatia’s onboarding process from his previous role as GM at Enchanted Isle in Hollywood, Florida, which recently joined Vacatia. That institutional knowledge helped smooth the transition. Vacatia adapted to the resort’s unique operational needs, helping the team maintain consistency for owners and exchange partners. One unique aspect was Cold Spring’s non-standard interval calendar, which deviates from the industry norm by having only 50 weeks.

Perhaps most notably, rental revenue increased by an astonishing 142% since Vacatia took over. Stoyer attributes this to the company’s savvy understanding of the vacation rental market, dedicated rental management team and seamless integration of technology that supports both staff and guests. “Technology is going to be your friend,” he advises other resorts. “Make sure the management company understands the rental market and can truly fill those gaps for you.”

While the staff remained the same, morale improved as the new tools streamlined operations. “It opened up efficiencies and our employees’ ability to focus on guest satisfaction,” Stoyer said.

Gold Point: Renovations and Resilience at High Elevation

At Gold Point Resort in Breckenridge, Colorado—perched at a breathtaking 11,000 feet elevation—the shift to Vacatia was a result of its need to partner with a company focused on challenges faced by legacy resorts. The HOA board interviewed 10 management companies and chose three finalists before selecting Vacatia. Their criteria included technology leadership, rental strategy, and the ability to respect the resort’s governing documents.

“We needed a management company that was forward-looking,” said HOA Board President Dr. Kirtland Speaks. “Vacatia was the only one thinking about Airbnb, VRBO, and what the timeshare model looks like in the future.”

Now in their fourth year with Vacatia, Gold Point has seen extensive improvements. Renovations are being systematically completed across the resort’s 48 units across eight buildings, funded by reserve accounts but managed by Vacatia. Speaks noted that the company handles everything from planning to contractor oversight. “They keep us informed during the entire process,” he said.

Operations, too, have reached new heights, and guest reviews reflect it. Gold Point is now the No. 1-ranked condominium resort in Breckenridge on Tripadvisor. “We’re the smallest of all the places, but we’re No. 1,” Dr. Speaks added. “There is some stiff competition in our area.”

Importantly, the transition preserved board autonomy. “We were all worried that Vacatia would come in and steamroll the board. That didn’t happen. It’s been a cohesive partnership.”

Neptune House: Tailored Response

Neptune House, a 23-unit seasonal resort on Block Island, Rhode Island, has a unique rhythm defined by ferry schedules, weather disruptions, and a tiny year-round population. After becoming dissatisfied when its previous management company had a change of ownership, the HOA board sought a company that would embrace the island’s idiosyncrasies.

According to board president Phil Totino, Vacatia stood out for its willingness to tailor its services. “We felt confident that the company’s staff would be highly competent and amenable to the particular needs of our resort,” he said. Totino said he was impressed by Vacatia’s leadership and was encouraged by strong references from other resorts under Vacatia’s management.

The changeover went smoothly, despite a hiccup when the previous company abruptly stopped processing maintenance fees well before the formal transition date. Vacatia’s accounting system is better aligned to how the resort is managed, and the board now has access to clearer financials and deeper data visibility.

Neptune House’s resort manager, its only permanent employee, adapted quickly, embracing the improved systems. Meanwhile, Vacatia’s communications support has elevated owner engagement with professional-grade newsletters and responsive service.

While Totino notes that it’s still early in the partnership, he sees Vacatia as “a 21st-century management company with robust systems and processes, delivered by an outstanding staff.”

Roadmap for Change

Despite differences in geography and size, all three resorts convey the same message: selecting a management company requires diligence, a clear understanding of goals, and a commitment to long-term collaboration. These boards retained autonomy while gaining professional partners to tackle rentals, renovations, reporting and more. Perhaps most importantly, all three resorts stress the value of choosing a company that treats them as a unique entity rather than forcing them into a generic mold.

Judy Kenninger heads Kenninger Communications and has been covering the vacation real estate industry for two decades.