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A World Away, Close to Everything

Just minutes from the charm of historic Jacksonville, and located conveniently between Medford and Grants pass, Starry Oak Ranch puts you close to Southern Oregon’s most beloved experiences — including summer concerts at the Britt Festival, acclaimed local wineries, boutique shopping in nearby historic Jacksonville, and award-winning dining — all while returning home to complete privacy, open skies, and peaceful vineyard views.

Private gated ranch in Southern Oregon wine country surrounded by oak trees
Starry Oak Ranch Chef Kitchen and Cozy Living Room Vineyard Vacation Rental with Views
Starry Oak Vineyard Retreat Woodrat Mountain Applegate Oregon Views
Starry Oak Vineyard Retreat comfortable luxurious bedding short term rental outside Jacksonville Oregon
Starry Oak Vineyard Retreat Sunset by the Fire Pit and Mountain Views

Property Highlights

Gated Access & Total Privacy – Feel worlds away, yet minutes from town.
Close to Jacksonville & the Applegate Valley – Explore historic streets, vineyards, trails, and local charm just a short drive away.
High-Speed Internet – Stay connected while enjoying off-the-grid peace.
Incredible Stargazing – With minimal light pollution, the dark skies at Starry Oak are perfect for viewing constellations and meteor showers.
Unforgettable Sunrises & Sunsets – Watch the sky transform from every window and patio.
Adventurer’s Basecamp – Located at the base of Woodrat Mountain, a paragliding hotspot.
Modern Convenience – Enjoy the luxury of DoorDash and Instacart delivery services right to your mountain escape.

This is the most beautiful place imaginable. The interior is amazing, the chef's kitchen has all the top notch appliances you could ever ask for and everything was very clean and well laid out. The furniture is gorgeous and so comfortable and the bathrooms were immaculate. The grounds are breathtaking and a great place to walk. It is hard to believe that we could walk as a family through vineyards. The surroundings were spectacular with the nearby hills and countryside. The neighbors were friendly, helpful and a lot of fun to meet.
We had space to gather as a family, cook gourmet meals and make memories that will last for years.
It is not far from Jacksonville which is a fun little town with great shops.
We would love to go back to make more memories in this beautiful place.

Tyler, Oak Harbor Washington - Airbnb

Please
Bring 
Your
Furry 
Friends
Along

Dogs might love this place more than people do.

Vacation rental with gated privacy and dog-friendly amenities at Starry Oak Ranch
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