Keys, Please: Healdsburg Cottage and Pilates Studio

This Keys, Please feature involves a fun bit of backstory. Before I was the owner and host of Harold House I was just a single girl who had recently moved across the country from New York City to San Francisco and was becoming familiar with different parts of wine country. To be honest I don’t even know how I first heard of Healdsburg, but it was on my list of towns to visit. Given that my competitive sport is creating Airbnb wishlists I had bookmarked a dreamy place with light and artful interiors, a fireplace and french doors that led outside to a shared backyard and sitting area. What really did it for me is that there was even a shed with a pilates studio (my exercise of choice).

The only problem was I discovered it in April of 2020, when the last thing people were doing was traveling to a stranger’s vacation rental during the early days of the pandemic. So it sat on my wishlist until finally I was able to enjoy it for a weekend away this summer, more than three years after I initially found it and after becoming a host myself. My stay was part practical (I needed to be in town to turnover Harold House which was occupied until the next guest arrived) and the other part full circle, wanting to stay in one of the places that first inspired me to host in Healdsburg.