How to Make Loyalty Programs Work in Vacation Rentals: An Inside Look at Red Cottage’s Membership Program

Meet Matthew Orley, CEO of Red Cottage, a premier platform and vacation rental brand for unique stays across the Northeast.

Matthew's journey with Red Cottage started as a guest in 2012. Captivated by the brand's consistency, unique portfolio, and potential, he acquired the business in 2022. Now, as the owner, Matthew is on a mission to transform Red Cottage into a regional powerhouse, known for its high-quality homes and exceptional guest experiences.

In this episode, Matthew and I discuss:

• The origin story of Red Cottage and its evolution over the years
• The innovative membership program Red Cottage launched, which is designed to foster loyalty and make last-minute getaways even more 
• Insights into acquiring vacation rental management companies — Red Cottage just acquired Posto
• The importance of maintaining brand authenticity while scaling
• The biggest opportunities for hospitality entrepreneurs right now to build, buy, and sell businesses 
• And so much more 

Alright friends, without further ado, get ready to meet Matthew.

Discover Red Cottage

Connect with Matthew on LinkedIn

This episode is brought to you by Hudson Creative Studio — the leading web design agency for vacation rental managers.  Hudson Creative  is offering a special deal for Behind the Stays listeners. When you mention Behind the Stays during your discovery call, you’ll get 10% off any service level option.

If you’re serious about taking your hospitality brand to the next level, head over to HudsonCreativeStudio.com/behindthestays. Trust me, Eli and his team will make your website something truly special. 

And don’t forget to listen to our series, "Unlocking the Secrets of Successful Hospitality Websites," which we’ll link in the show notes below, for a deep dive into what makes these guys the best in the biz.

Want to book a consulting brainstorm with Zach?

Send him an email directly at zach@staywatch.ai or complete this payment link and get immediate access to his schedule where you can book some time with him!

About the Show

Behind the Stays is brought to you by StayWatch — the internet's best resource for deals on Airbnb, Vrbo, and Booking.com. You can subscribe, for free, at www.staywatch.ai

Behind the Stays is hosted by Zach Busekrus, Co-founder of StayWatch, you can connect with him on Twitter at @zboozee or on LinkedIn.