Welcome to Strategic Stays
Smarter, Boutique Property Management.
At Strategic Stays, we do things differently. As experienced property investors and owner-managers, we understand the frustrations of overpriced cleaning and management fees. That’s why we’re committed to providing hands-on, personalised service that keeps your costs low and your returns high.
Our boutique approach means we manage a select number of quality properties, allowing us to stay focused, detail-oriented, and results-driven. We’re not just another property management company—we’re fellow investors who get it.
Smart & Strategic
Strategic Stays was founded by Joel Crosswell — a property investor with a deep understanding of the short-term rental space. What started as a personal drive to maximise returns on his own property quickly became an obsession with perfecting the guest experience and boosting performance through hands-on, data-led management.
What started with a single property — Cottage on Lords — soon turned into a hands-on crash course in short-term rental success.
Joel spent countless hours digging into market trends, testing pricing tools, and figuring out what makes guests come back. It wasn’t always smooth sailing, but every decision was focused on one thing: getting more bookings, better revenue, and creating stays people would actually rave about.
Now, by listing properties across Airbnb, Booking.com, VRBO and Expedia and combining that with and local insight — Strategic Stays consistently delivers strong results for both owners and guests.
After the success of Cottage on Lords, Prince Street Cottage was added to the portfolio and has since become one of Orange’s top-performing short-term rentals. Strategic Stays continues to grow, offering owners a boutique management solution that’s transparent, cost-effective, and built for long-term success.
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.
Dynamic Pricing
Use of industry-leading tools to maximise occupancy and revenue.
Guest Communication
24/7 support with fast, friendly responses.
Personalised Recommendations
Local insights to enhance the guest experience.
Optimised Listings
Tailored content and visuals to attract more guests.
24/7 Support
Reliable assistance to ensure guest satisfaction.
Automated Messaging
Clear, welcoming, and informative communication at every stage.
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!
Whether you’re a guest or a property owner, we’d love to hear from you. Reach out for more information or to discuss your property management needs.