Welcome to Strategic Stays
Smarter Short-Term Rental Support.
At Strategic Stays, we help homeowners and investors get more out of their short-stay properties without the complexity or cost of traditional agencies. We’re not agents—we’re hands-on operators who know what makes STRs thrive in the real world. From listing creation to guest communication, we handle the details so you don’t have to.
We only work with a select number of properties at a time, which means you’re getting boutique-level support, not just another cookie-cutter service.
Smart & Strategic
Joel Crosswell, Owner/Founder of Strategic Stays
A property investor who knows firsthand what makes short-term rentals work and what doesn’t. What started as a personal mission to improve returns became a full-blown obsession with the guest experience, systemisation, and smarter ways to operate. It all started with his first family home Cottage on Lords. That property became a crash course in pricing, guest behaviour, reviews, and market data. Every lesson was put into practice. More bookings. Better reviews. Stronger returns.
Since then, Strategic Stays has grown by doing one thing well delivering better results through fewer distractions. Small on purpose, every property gets tailored attention, clear systems, and smart, hands-on support. It’s not about volume. It’s about performance and owners who actually know what’s going on.
Our Featured Stays
Prince Street Cottage - Pet Friendly
Prince Street Cottage is a beautifully restored, heritage-listed Edwardian home in the heart of Orange. Blending 1890s charm with modern, eco-conscious living, it’s proudly carbon positive—powered by solar and dual home batteries (18.8kW & 13.3kW). Includes a Tesla Type 2 EV charger. Enjoy heritage elegance with sustainable comfort.
Cottage on Lords | Pet friendly
This beautifully renovated 1941 cottage offers everything you need for a relaxing getaway. Featuring three spacious bedrooms, a modern bathroom, a fully equipped kitchen, and a laundry, it’s the perfect retreat for families, friends, or couples.
With an open-plan layout, guests can enjoy entertaining, unwind with a glass of local Orange wine, or stream their favorite shows on our 55-inch Smart TV with multiple streaming apps.
Lower Fees
Transparent and competitive pricing without hidden costs.
Personalised Recommendations
Local insights to enhance the guest experience.
Optimised Listings
Tailored content and visuals to attract more guests.
Automated Messaging
Clear, welcoming, and informative communication at every stage.
Dynamic Pricing
Use of industry-leading tools to maximise occupancy and revenue.
why choose our stays
Curated Stays
We manage a select number of quality homes, carefully chosen for comfort, cleanliness, and style.
Local Hosts
We're based nearby and offer fast, friendly support whenever you need it — no call centres here.
Best Price, Direct
Book through our website for the best rates — no hidden platform fees or third-party markups.
Home Comforts
Enjoy fully equipped kitchens, plush bedding, fast Wi-Fi, and everything else that makes a place feel like home.
Seamless Check-In
Contactless check-in with smart locks or key safes, plus clear instructions for a stress-free arrival.
Top Regional Locations
Stay close to wineries, cafes, national parks, and local gems — perfect for both adventure and relaxation
What Our Clients Say
"Strategic Stays transformed our property’s performance. Lower fees, better service, and consistent bookings—it’s a game-changer!"
Total Booking
Happy Clients
Years of Experience
Awards Winning
Frequently Asked Questions?
Let’s Chat!
Got a question or thinking about getting started? Reach out, we’d love to hear from you. Whether you’re a guest or an owner, we’ll point you in the right direction.