Come Work With Us

The world deserves more hospitality. That includes the people who deliver it.

Cascadia Getaways is hiring. We're an Oregon-only, employee-owned vacation rental company — which means the people who care for our 110+ homes aren't just employees, they're the heart of the company. We're built around the idea that better outcomes for owners and guests come from a team that's actually invested, supported, and respected. That's not marketing language. It's how we run the place.

Or scroll down to learn what working at Cascadia Getaways is actually like.

Cascadia By the Numbers

What Working at Cascadia Getaways Is Actually Like

We talk about hospitality a lot on the rest of this site. Here's what it looks like internally — the parts you don't usually see on a careers page:

Your manager is a co-founder, not a layer of org chart.

Stephanie Whitmore, our co-founder, leads operations. She came up through military logistics and the kind of administrative rigor you only get growing up in a medical insurance coding business. That means our operations are tight — but it also means when something goes sideways, you can reach a co-founder or empowered manager who can actually make decisions, not a manager who has to escalate.

We're not chasing scale. We're building a craft.

Most vacation rental companies are owned by private equity, venture capital, or both. Their funds need 30% returns on capital, which means cutting corners on the people who do the work. We're employee-owned and Oregon-only. We don't have outside investors demanding growth at any cost — which means we can pay attention to the work and the people doing it.

Your time is respected.

Cleaners get clear schedules, not last-minute scrambles. Maintenance leads get the tools and supplies they need before a job, not after. Guest support has actual playbooks, not just "figure it out." We use AI internally so our humans can spend more time on the parts of hospitality that matter — and less time on tickets, paperwork, and chasing vendors.

You're treated as a professional.

Stephanie's team takes pride in being skilled at what they do — and we hire and pay accordingly. We're not a gig platform. We're not a body shop. If you're great at cleaning, maintaining, fixing, hosting, or organizing — we want to build a long career with you.

People stay.

Industry turnover for housekeeping and operations runs 6–12 months at most companies. Some of our teammates have been with us 8+ years and counting. That's not an accident. That's the point.

What We Hire For

We're an Oregon-only, mostly hourly, hospitality-and-operations company. The roles we hire for most often:

• Property Care Specialists / Turnover Specialists — the people who actually make a stay great

• Maintenance Technicians — handy, problem-solving, vendor-coordinating

• Inspectors — quality control after every clean

Our Values (and How They Show Up Internally)

We're always meeting great people — even when we're not actively hiring for a specific role. If you have a passion for hospitality and the kind of work ethic that comes from caring about the details, send us your resume. We hire when the right person shows up, not just when a seat opens.

Apply

Tell us a little about yourself. We respond to every application personally — no auto-rejection emails, no ghosting.