Pinemark: 35 years of doing hospitality their own way

Pinemark’s story began more than three decades ago in the early 1990s, when the grandmother of current owner Jason was told a hotel in the area simply wouldn’t work.

“They did a feasibility study and said, ‘There’s no way. You can’t do a hotel here,’” explains General Manager Courtney Cronin. “And she said, ‘Well, yes I can.’ And she did.”

More than 35 years later, that independent spirit still defines the family-owned property. Rebranded as Pinemark in 2021, the 64-room hotel, guest house, and event space combines decades of hospitality experience to create authentic, personal stays built around its promise to ‘rest easy with local hospitality.’

For Courtney, that means having the freedom to be “irrationally hospitable” — anticipating guests’ needs, trying new ideas, and going the extra mile without a corporate playbook getting in the way.

It’s an approach rooted in the belief that independent hotels keep hospitality personal, distinctive, and connected to the communities around them.

When Pinemark developed its new identity, the team deliberately created a brand that could grow alongside the business without sacrificing its independent character.

Pinemark ventured into hospitality management, including a luxury vacation rental and other properties managed under Pinemark Hospitality. The goal is to take the expertise developed in the hotel business and apply it to vacation rentals, bringing what Courtney describes as a more hotel-like, elevated level of hospitality to the segment.

And as the Pinemark brand evolves, so too has the technology supporting it. “We liked that Cloudbeds was kind of an all-in-one product versus trying to hodgepodge together a channel manager and all these different things,” says Courtney. “It really enhanced our operations when we made that change.”

Over time, Pinemark has expanded its use of Cloudbeds to include Groups, Revenue Intelligence, and Guest Experience, while also preparing to adopt additional functionality.

“You can’t overstate just how convenient it is for it to all be in one place.”

Revenue management is particularly important for Pinemark because of the property’s significant group and event-based business. Sometimes the team knows well in advance when an event will drive demand. Other times, demand starts moving before the reason behind it becomes obvious.

Cloudbeds Revenue Intelligence helps Pinemark spot those opportunities. “It’s nice to have Revenue Intelligence flagging those dates for you without any manual work on your part,” Courtney explains. “There’s an uptick in booking velocity, or you’re at a higher occupancy, and you need to adjust your rate for these dates.”

Instead of relying solely on someone noticing a change and reacting manually, the team gets additional intelligence to help identify dates that deserve attention. Courtney describes the functionality as “really accurate and thorough.”

For an independent property balancing day-to-day operations with groups, events, guest experience, and revenue strategy, that added visibility makes it easier to focus attention where it matters most.

Pinemark is also using Cloudbeds Guest Experience and Whistle to automate guest communication.

The team has built automations that help it stay in contact with guests throughout their journey, while text messaging creates a direct communication channel even when the original reservation came through an OTA.

“Even if they didn’t start on your property, you could convert them for their next stay,” she says. “I think that has been one of the biggest value adds for us.”

Automation also helps remove simple, repetitive questions from the front desk. A guest who wants to know the checkout time, for example, can get the information through a quick text rather than calling reception.

“A simple text message — ‘What time is checkout?’ — stops the phone call,” Courtney says, helping keep reception staff “face-to-face with guests versus answering easy questions that could be done differently.”

It’s a small distinction, but one that captures Pinemark’s philosophy: technology should handle the things technology is good at so people can spend more time doing the things that make hospitality personal.

Thanks to Cloudbeds’ intuitiveness and Cloudbeds University, Pinemark can reduce the amount of time it spends teaching employees how to operate hotel software.

“Cloudbeds University does a lot of the work for you,” she explains. “We get to spend more time training on hospitality and guest-facing skills versus teaching somebody how to use a program.”

The same resources help Courtney stay current as Cloudbeds introduces new functionality, allowing her to learn the product before bringing those capabilities to the wider team.

She also values having a platform that continues to evolve alongside the hotel. “That’s another really good thing about Cloudbeds — they do grow and keep up,” she says. “We’re never wishing that a feature existed. When you want something, great, because they’re working on it.”

Today, Pinemark is simultaneously protecting what has made the property successful for more than three decades and exploring what its independent hospitality model could become next.

That means managing the original 64-room hotel, groups and events, guest communication, revenue strategy, an expanding management business, and new accommodation concepts — without losing the personal hospitality at the heart of the brand.

It’s also why Courtney has recommended Cloudbeds to other independent properties in the area, including new hoteliers implementing their first PMS.

“There’s so much that goes into managing a property,” she says. “If you can make your tech stack the easy part, it gives you more time for the other things.”

For a property proudly “independent through and through,” those other things are what matter most: knowing the guest, anticipating what they need, experimenting with something new, and having the freedom to go the extra mile.