The Calderwood Inn sits just a few blocks from Healdsburg Plaza in a restored Queen Anne Victorian mansion that feels like stepping into another era. The place has real character—ten rooms each with private bathrooms, and you’re surrounded by lush gardens where you can actually wander around. There’s a bocce ball court if you want to toss some balls, and a lily pond that’s nice to look at while having your morning coffee.

They allow one dog under 50 pounds in three designated suites: the Pezzi King, Mosaic, and St. Anne’s. There’s a $50 pet fee per stay. Your dog needs to stay leashed while on the property, and you can’t leave them unattended in the room—which makes sense in a place this nice. If your dog barks excessively or causes problems, they’ll ask you to kennel the dog or leave, so this works best if your dog is reasonably calm and settled. They don’t allow cats, only dogs.

What actually works well here is the location. You get a fresh breakfast prepared every morning, and the inn arranges wine tastings at Wilson Artisan Wineries during your stay, which is a nice bonus if you want to spend time tasting without worrying about driving. Being close to the plaza means you’re near shops, restaurants, and galleries. The proximity to local parks is genuinely useful if your dog needs exercise and you want to explore the Healdsburg area on foot.

If you’re traveling with a dog that’s content to relax in a room or lounge around the gardens rather than needing constant activity, this Victorian setting works well. The place has personality beyond just being a generic hotel, and the central location means you don’t feel like you’re stuck at the property. Dogs tend to relax better when their people are relaxed, and staying somewhere with character like this actually makes a difference in how the trip goes.