With National award-winning architecture, this Mediterranean compound in Philo started as a modest rural homestead and TV repair shop before being transformed over the past 20 years by designer and lifestyle entrepreneur Jim Roberts, who now prefers being called “The Groundskeeper” for the property. Walking through the courtyards and arcades, you’ll immediately notice how the open-air design creates natural gathering spaces—the kind of place where you can sit with your dog without feeling rushed or out of place.

The west-side arcade leads through wooden gates to the tasting rooms for Bink Wines and Signal Ridge Vineyards, so you can sample local wines while your dog rests nearby. The cottage gardens thrive along this same arcade, and during summer and fall a working culinary kitchen garden supplies much of what the property needs. It’s the kind of detail that tells you someone actually cares about what happens here.

Dogs are welcome in two guest quarters: the Garden View and The Living Room. Both offer a more relaxed alternative to typical hotel rooms, with the added benefit of being part of this carefully considered landscape rather than feeling like you’re just renting a standard space. The setting works well for dogs who appreciate quiet—you’re in wine country without the crowded tasting room atmosphere, and there’s actually space to move around.

The property sits in Anderson Valley wine country, so if you’re planning a wine-focused trip and want somewhere your dog can stay comfortably, this is a genuine option rather than somewhere that merely tolerates pets. The architecture and gardens are worth seeing even if you’re just passing through Philo. Just remember to clean up after your dog, as the grounds are clearly maintained with care.