What inspired you to create Cascadia Getaways, and how do you select properties and locations?
After helping build Vacasa through its IPO, we recognized the need for a management solution that blends advanced technology with genuine local care. We saw a gap between massive, scaled companies and small local managers lacking technology and innovation. Cascadia Getaways bridges this, offering the revenue capabilities and operational efficiency of large systems alongside the boutique, Oregon-only, homeowner first experience of a local team. We are purely Oregon focused, free from venture capital influence, and committed to strong hospitality for both our homeowners and their guests across the state. We put as much attention on property selection as we do partner selection. We look for properties in the Mt Hood, Wine Country, Coast or Black Butte area. If there is a good homeowner partner fit outside of those areas we evaluate our ability to service as we do have a strong contractor network we lean on as well. Another element that sets us apart is our effort to develop company values that create opportunities and a great quality of life for our staff. The cleaning and maintenance professionals in the vacation rental industry do the work that AI will never replace and they deserve to enjoy the rewards of their hard work.
What sets Cascadia Getaways apart in the Oregon vacation rental market?
We saw a clear opportunity after helping scale a major national firm to its IPO: maintaining high-level performance without sacrificing local service. We combine the advanced revenue and marketing strategies, AI tooling efficiencies and technology of a large company with the personal, employee-first commitment of a boutique, Oregon-exclusive manager. Since we have no outside venture capital pressure, our focus is entirely on sustainable growth and delivering a high-touch experience for our homeowners and their guests. We have seen first hand the impersonal and negative changes that venture capital can bring to the business, especially for the destination communities where most vacation rentals exist. We believe in being great community business members in the locations where we operate, and this plays out with our support for local businesses and non-profit organizations.
What trends are you seeing in vacation rentals and regional travel for 2026?
The vacation rental market is entering a new phase in 2026, and Oregon is well positioned. After years of rapid growth and a choppy 2025, supply is stabilizing, travel demand is holding, and opportunities are getting clearer. Guests are booking closer to arrival, prioritizing design and amenities, and rewarding well-run homes with higher rates and better reviews. Markets like Mt. Hood, the North Coast, and Wine Country continue to outperform because they’re drive-to, experience-driven, and resilient. This isn’t a hype cycle anymore—it’s about strategy, pricing, and execution. On the property level, guests continue to look for more hotel-like hospitality such as professional 24/7 guest communication and concierge type services. Also this prediction–saunas will be the new hot tub.
For homeowners considering turning their property into a short-term rental, what are the top three things they should know before getting started?
- It’s a hospitality business, not passive income. Guests expect clean, comfortable, well-designed homes and will judge your place against the best stay they’ve ever had.
- Pricing changes constantly. Successful rentals adjust rates based on seasonality, demand, and events — setting one price and walking away usually leads to lost income.
- Guest experience matters as much as location. Great photos, thoughtful amenities, and “vacation-ready” design often outperform better-located but underwhelming homes.
- Small upgrades can drive big returns. Things like saunas, hot tubs, fire pits, fast Wi-Fi, and good beds directly impact bookings and reviews.
- Experience and guidance matter. Owners who work with experienced managers tend to avoid costly mistakes and earn more over time.
For investors hoping to purchase a second home/vacation rental this year, what are the top three things to look for in a property?
- Choose a location people actually travel to year-round. Drive-to destinations like the Oregon Coast, Mt. Hood, and Oregon Wine Country tend to be more resilient and book consistently, even in softer travel years.
- A home that can stand out, not just fit in. Properties with good layouts, outdoor space, and room for upgrades (hot tubs, fire pits, great design) outperform generic homes. Find value-add opportunities like a den or garage conversion to a bedroom or game room.
- Numbers that work today, not just on paper. Look at realistic rental income, operating costs, and seasonality — not best-case scenarios or peak-summer assumptions.
What surprises homeowners most about renting their properties for the first time?
- Safety and liability are much bigger than expected. Things like fire escape ladders, smoke and CO detectors, camera laws, and guest safety standards catch most owners off guard — and the legal risk is real if something goes wrong.
- There are more rules than people realize. Permits, taxes, insurance gaps, privacy laws, and local regulations can vary by city and state, and missing one can lead to fines or worse.
- It’s more hands-on than it looks. Guest questions, maintenance issues, and problem-solving don’t follow a 9–5 schedule, and small mistakes or lack of responsiveness can quickly turn into bad reviews.
- This is a competitive Space. It takes consistent work on many fronts to properly position a rental home to stand out and consistently attract guests.
This is where working with an experienced manager helps — guiding owners through safety, compliance, and day-to-day operations so the property performs well and everyone sleeps better at night.
What sets you apart from other vacation-rental or property-management companies?
What sets Cascadia Getaways apart is that we manage homes like assets and hospitality businesses, not just listings. We’re deeply data-driven on pricing and marketing, but we pair that with real human judgment shaped by multiple market cycles. We’re also safety-first and compliance-focused, helping owners avoid the risks most don’t realize exist until it’s too late. Add in our deep Oregon market knowledge and a focus on guest experience, property care and technology, and the result is higher-performing homes with fewer surprises for owners. Cascadia Getaways has strong company values that deliver great results for the homeowners we serve. Our goal is to grow thoughtfully so that homeowners are always able to connect with decision makers in the company.
For those who are already thinking about spring break travel, how far in advance are your rentals typically booked?
Spring Break bookings vary a lot by market and by home type, but we’re already seeing early movement. In places like Seaside, roughly 10% of homes are already booked, and that early demand is concentrated in the most desirable inventory — especially oceanfront and larger homes, which tend to book well ahead of market averages. Historically, Seaside has a median Spring Break booking window of about 20–25 days, while Mt. Hood and Wine Country tend to book 30+ days out. Our rule of thumb: if you have your heart set on a specific home or location, it’s best to book before January or at least two to three times the average booking window. If flexibility matters more than the exact home and you’re looking to save, waiting until one to two weeks before arrival can sometimes uncover good value, especially on smaller or less specialized properties.
Curious whats available? Booking on Cascadia Getaways saves you on third party fees which can be between 15% - 20%. Book direct, save money and support a local business. If you still like to use Airbnb’s interface consider using Directo to find those properties directly or search the listing description online to find the direct listings.
