About Cascadia Getaways
A leadership team made up of three Oregonians with a decade of vacation rental experience, united by the belief that the world deserves more hospitality.
We're Cascadia Getaways. We manage 110+ vacation homes across Oregon's most beautiful destinations — Mt. Hood, the Oregon Coast, and Oregon’s iconic Wine Country — and we bring more than a decade of experience in short term rental focused hospitality to the office every day. We're local, employee-owned, and obsessively focused on our amazing state. No national ambition distractions. No private equity control. Just three co-founders, a tenured team, and a real Oregon address.
If you're a guest, this page is for you to know who you're trusting with your trip. If you're a homeowner, this page is for you to know who you're trusting with your home and investment. Either way, we're glad you're here.
Cascadia Getaways By the Numbers
110+ | 10+ | 3 | 40% | 8 yrs |
Oregon homes managed | Years in Oregon vacation rentals | Markets we know cold | Direct bookings (industry avg: 10–15%) | Some teammates have been with us this long |
How Cascadia Started
Ryan, Gerard, and Stephanie didn't meet in a conference room. They met in the work — across years and multiple companies inside the Oregon vacation rental industry. Ryan spent a decade in revenue management, including building forecasting tools for one of the country's largest vacation rental managers. Gerard brings more than 20 years of hospitality leadership and owner partnership. Stephanie brings operational discipline forged in the U.S. Military, the administrative rigor of growing up inside her mother's medical billing business, and the project management instincts of a builder's daughter who's spent real time on a job site. Together, they've built a company that runs on hard-won expertise in every corner of the business — revenue, relationships, and the homes themselves.
Three different operators. One shared frustration: too much of the vacation rental industry had drifted away from actual hospitality. Owners felt like accounts. Guests felt like transactions. Teams felt like cost centers.
So in 2024, they started Cascadia Getaways. Oregon-only. Employee-owned. Built around one operating principle: the world deserves more hospitality. We're still here, still independent, and still growing alongside the owners and homes we care for.
Meet The Co-Founders
Ryan Rabideau
Co-Founder & Revenue
Ryan has spent over a decade in Oregon vacation rentals. Before founding Cascadia, he led revenue optimization and built forecasting algorithms at Vacasa — work that's now baked into the pricing strategies of tens of thousands of homes across the country. He's spoken at the VRMA conference on OTA distribution and has spent his career in the analytics, pricing, distribution, and AI booking corners of the industry. He's built AI booking tools and other managers with one of the first AI booking platforms in vacation rentals, building the connectors that let AI agents discover and book properties on behalf of guests.
At Cascadia Getaways, Ryan is your revenue strategist. He sets nightly pricing strategy, OTA distribution mix, and the AI infrastructure that lets our team spend less time on tickets and more time on hospitality.
Gerard Lester
Co-Founder, Business Development and Homeowner Communications
Gerard brings 20+ years in partnerships, owner care programs, and hospitality leadership. His career has been built on the idea that long relationships outperform short transactions — and at Cascadia Getaways, that's exactly what he protects. He's the direct line for our homeowner partners, and the reason our owner reviews tend to use words like patient and flexible and understanding.
Stephanie Whitmore
Co-Founder & Operations
Stephanie is the operational backbone of Cascadia Getaways. She's an 8+ year licensed Oregon STR property manager — but the more interesting part of her resume is what she did before that. She served in the U.S. military, where logistics aren't a slogan but a survival skill. And she grew up inside her mother's medical insurance coding business, where every claim required forensic-level documentation or it didn't get paid. That's the discipline she runs Cascadia operations with: nothing dropped, everything documented, accountability all the way down.
It's why Cascadia owners write reviews about Stephanie specifically. "Stephanie is the best property manager I have ever had. She always has an answer when I have questions." (— Dee, Lincoln City Homeowner.) That's not luck. That's the standard.
The World Deserves More Hospitality
That's our operating principle. This concept decides who we hire, which homes we accept into our portfolio, and how we treat the people on every side of a stay — guests, homeowners, teammates, vendors, neighbors. It also turns into five specific commitments we hold ourselves to:
We assume best intentions.
Whether it's a guest, a homeowner, or a teammate, we lead with trust and openness. Proof: When a guest reports damage, our default is to believe them and resolve it — not to interrogate them. (We document carefully because Stephanie's team always documents — but we lead with grace.)
We always do the right thing.
From how we care for homes to how we serve guests, we operate with honesty, transparency, and heart. Proof: All fees are transparent at checkout. No surprise charges. If we made a mistake, we tell you and fix it — we don't bury it in a statement footnote.
We act like owners.
Our team treats every property as if it were their own. Proof: Our inspectors walk every home the day of guest arrival, even after a home has already been inspected. Our maintenance team has a maintenance plan for each home and is invested in caring for our properties.
We are stewards of the community.
Our neighborhoods matter. We partner with local businesses, respect our neighbors, and contribute to the places that make Oregon special. Proof: We show up to local late night meetings. We have been tour guides and adventure guides–we even ran a campervan rental business helping people explore our great state. Our local guides don't list chain stores. Our team shops, eats, and lives in the markets we manage. When a neighbor calls, our team — not a national hotline — is the one who picks up.
We are here for the long haul.
Locally owned, employee-powered, sustainable both environmentally and economically. We're not chasing trends. We're creating a legacy. Proof: No outside investors. No private equity. Some of our teammates have been with us for 8+ years. We grow when our owners and our homes do — not when a fund needs a quarterly print.
What are people saying?
From our homeowners
"The Cascadia Getaways team is incredibly responsive and goes above and beyond with cleanliness and maintenance. They've helped us remedy everything from roof leaks to trees falling on our property." — Jesse, Gearhart Homeowner
"They have been phenomenal in all aspects of management. Quick response time and couldn't be happier with marketing. Usage is up significantly from other providers I have used." — A.Jay, Oregon Coast Homeowner
"Cascadia Getaways has been a fabulous partner for us. They have spent time to get to know us and our place, and have worked hard to ensure that guests have the highest quality experience when staying in our home." — Mark, Central Oregon Homeowner
From our guests
“We had a great stay. It was clean and quiet. We loved being outside the hustle and bustle of Seaside but close enough to still enjoy it. The house is laid out well. The huge couch made for comfortable movie nights (along with a large selection of DVD’s) and the kitchen was excellent for cooking meals. Would stay again!”
“Beautiful home in government camp. Lots and lots of beds, mostly twin beds and 3 Queens. The Main bedroom with bathroom is on the main floor. The two other queens are up the stairs. The one to the pest has a door and the one to the right has a door but then there are 6 twin beds beyond it - so if the kids wake up that might not be the bed to choose. There’s also a game room back that way. The bathrooms are all on the bottom floor so make sure the kids don’t drink too much before bed or depending on age you might need to wake up and escort them to the bathroom. The living room fire place is very nice. There’s one on the dining room too that we didn’t use. Large space - a bit like a labyrinth but fun. Two minute walk to Govy General (grocery store) and restaurants. 5 min walk upward to one trail. Lots of trails nearby. Skibowl West has a level 3 fast charger for EV users. They also had helpful add-ons like coffee, etc. Definitely recommend the place.”
“Fantastic space. A quintessential A-frame experience. Really enjoyed the space with a family of four. The sauna is top notch.”
“Obsessed with this place and will stay again and again! Positive: Loved being so close to the beach and within walking distance to everything! The room had the most beautiful view of the ocean! Added bonus was having a pool & sauna too! Will definitely stay again!”
“This was a repeat stay for us and our 2nd grader. Home is in a great location for us and we alway see deer in the backyard. Access to the garage is a handy feature and they provide yummy coffee beans &grinder as well as good size coffee mugs (not as common as you'd think). We could also tell the hosts acted on feedback from our previous stays and they continue to communicate quickly and kindly. Thank you!”
Join the team
Have a passion for hospitality and looking for a new opportunity? At Cascadia Getaways we have learned by putting people first, results always follow. We are currently looking for passionate hospitality professionals for operational and housekeeping careers. If you are interested let us know!
