Today we’d like to introduce you to Jennifer Ober.
Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
We are Jennifer Ober and Gregory Dunham, the owners and managers of a unique and curated collection of vacation rentals in Wimberley, TX. We didn’t set out to be in the hospitality business, but we’ve found we have a knack for it!
For Gregory hosting just comes naturally. His mother’s career as a foreign student advisor at UH and Rice meant that his childhood home was never without an international guest. They hosted 14 year-long high school exchange students and hundreds of graduate students from around the world. After studying philosophy at Trinity, Gregory moved out of state working for art museums and learning the woodworking trade, but the gentle tug of the gorgeous Hill Country brought him back home to Texas.
Jennifer, who studied studio art at UT Austin, was the art teacher at AISD’s beloved Maplewood Elementary for 10 years before meeting Gregory and moving to the beautiful Wimberley countryside. With a passion for youth art, Jennifer wasn’t ready to leave teaching altogether and began teaching creative summer camps in her Wimberley studio. That evolved into becoming a founding member of local non-profit, projectART Wimberley, which supports WISD art programs and brings quality art and art programming to area youth in the ARTSPACE Gallery.
Our shared passion for travel, for art, for creating beautiful spaces, and for hosting visitors turned out to be the perfect collection of qualities for our little vacation rental business. Vacation Wimberley is a passion project for us. Our guests choose our spaces for everything from vacations, to anniversaries, honeymoons to wedding nights and we are deeply honored to host each and every one.
We all face challenges, but looking back would you describe it as a relatively smooth road?
Coming from other fields of study and work we found ourselves on a quick learning curve as we started out in the vacation rental world. We opted early on to manage a handful of homes for friends and community members that chose to temporarily rent their homes out as vacation rentals for a variety of reasons such as extended travel, serving in the armed forces, and living abroad. While we were honored to have this opportunity to grow our business while helping out these families, we’ve evolved over time to only operating the vacation homes that we also own. This gives us greater ability to control all of the aspects of a guests’ experience, from the products we stock to the design choices we make. Getting to this point feels like a dream and it’s such an honor to create spaces where so many forever memories are made. We host many wedding nights, anniversaries, honeymoons, family vacations, friend trips and more!
The other main challenge for us were the baby years, haha! We have two amazing kids, but owning and operating a small business through those baby years was certainly a challenge. When our first child was born, I remember Gregory helping a guest over the phone with directions while he was with me in the delivery room. We’ve grown, evolved, and added a small, amazing team since then, but we are absolutely still the faces behind Vacation Wimberley. It’s just refreshing to know you’re staying with people who care about your experience and are there to help if anything goes awry.
Can you tell our readers more about what you do and what you think sets you apart from others?
With Jennifer’s degree in studio art and professional experience as an art educator, she brings the creative eye to our spaces. Gregory’s experience in woodworking and art museums means that he can build and design so many things. He has an expansive wood and welding shop on our home property where he built the Airstream cabinets, built-in furniture, the Aframe custom cherry kitchen, the Edelweiss custom kitchen, most of the Moonshiner cabin, the custom kitchen and canopy bed in Three Graces Cabin and so much more. We work together like a team in every aspect of our lives and we have FUN doing it! We believe that the fun and creativity show in our spaces as well as in the experiences our guests have in them.
Alright so before we go can you talk to us a bit about how people can work with you, collaborate with you or support you?
We love community and collaboration! We are always open to a conversation about fresh and exciting ideas. We believe in supporting local businesses, good causes, and honorable organizations whenever we can. As a founding member of projectART Wimberley, Jennifer donates much of her time supporting their mission to support and enhance youth art opportunities. Gregory is a volunteer soccer coach for our local Wimberley Youth Sports Association. Our business, Vacation Wimberley, is a proud annual sponsor of the local Wimberley Pride march. We also work hard to be as green as we can be and are always looking for great eco-friendly products to stock in our vacation homes. We’re super grateful when folks refer friends and family our way and we think of that as the greatest honor in our business.
Pricing:
- Since pricing varies by season and property, it might be best just to refer folks to our website.
Contact Info:
- Website: https://vacationwimberley.com/
- Instagram: @vacationwimberley
- Facebook: https://facebook.com/vacationwimberley
- Youtube: Coming soon! We’re meeting with a film company on Monday for video content and can’t wait to see our places come to life with video!








Image Credits
Paige Wilks – family photo
James Ruiz – Moonshiner Cabin interior w/red wall
Andrew Heatwole – night shot (La Petite Tiny House), creek shot (Edelweiss Creekside Home), & the shot with the sun peeking over the covered patio with hanging chairs (La Petite Tiny House)
James Goulden – Aframe, cabin interior shot with canopy bed (Three Graces Cabin), sunset cabin with fire ring (Bohemian Cabin), bathroom pic (Bohemian Cabin)
