Our short-term rentals are cozy, welcoming, and ready for you to make yourself at home. Each space is stocked with everything you need for a convenient and comfortable stay.
Hi there!
We’re Gay and Pressley Jessica, the mother-daughter duo behind StayInn Locally. Based on the beautiful Eastern Shore of Maryland, we turned our passion for hosting into a business dedicated to making short-term rentals stress-free for owners and unforgettable for guests.
What started as a love for creating warm, welcoming spaces has grown into a full-service, short-term rental management company that takes care of every detail. From seamless guest experiences to maximizing property owners’ revenue, we bring a personal touch to every home we manage.
We’re committed to giving guests an outstanding stay while making hosting effortless for property owners. Our co-hosting services help hosts get the most out of their rentals while maintaining the highest standards of care.
A dedicated member and trustee of her church, Gay loves spending time with family, traveling to new places, and revisiting her favorite destinations.
When she’s not managing properties, you’ll find her crafting and enjoying life’s simple joys.
A classically trained singer with a rich background in opera and musical theater, Jessica has showcased her talent in stunning venues and national competitions.
Today, she brings that same dedication and attention to detail to her work as a speech pathologist in the healthcare field. Outside of her profession, Jessica enjoys traveling, spending quality time with family and friends, and relaxing by the water.
Every property we manage is a place to relax and feel at home. We love making sure our guests have everything they need for a comfortable stay.
We’d love to connect with you (promise, no spam!) and keep you in the loop on new getaway spots, exclusive discounts on StayInn Locally stays, and more. Plus, we’re always open to hearing how we can make your experience even better.
