Judy Madden
Guest Experience Director
Focused on making the planning process feel clear, warm, and personal from first question to arrival.
Our approach
Gypsy Cabins is built around a simple idea: the best getaways feel private, personal, and easy to step into.

Why we exist
A weekend away starts long before check-in. It starts when you decide you need a change of scene. Our job is to make everything from choosing a stay to planning the details feel clear and human.
That means fewer generic options, more useful context, and guest support that respects whether you want help planning every detail or would rather be left completely alone.
Principles
We would rather present a focused collection with a clear point of view than overwhelm guests with endless listings.
Guest care should remove friction, answer real questions, and let the traveler stay in control.
The best details are the ones that make a stay feel special without turning planning into another job.
Guest team
Our team structure is designed around stay curation, guest planning, and thoughtful service.
Guest Experience Director
Focused on making the planning process feel clear, warm, and personal from first question to arrival.
Stay Curator
Shapes the collection around comfort, setting, privacy, and the kind of experience each cabin supports best.
Concierge Lead
Helps guests translate a weekend idea into a practical, flexible plan with room for spontaneity.