Santa Rosa might not be the prettiest city in Sonoma County, but it is the largest and most convenient if you are planning a trip that does not only involve wine-tasting. The downtown area is full of department stores, restaurants, bars, hotels and office buildings, making it the only real city in the area. It's also the most kid-friendly place in the region, with an amusement park and other family-friendly activities.
It may lack the charm of smaller towns like Healdsburg, but it offers easy access to some of the most popular wine-tasting destinations.
There are plenty of hotels to suit every budget, from motels, to chain hotels, to luxury properties. However, don't expect to find top-notch boutiques like the ones you would find in Napa Valley, at least in the city center. There's a lot of everything in Santa Rosa, but stay in the area around 3rd Street and Santa Rosa Avenues for easy access to restaurants and shops. If you prefer more intimate properties surrounded by the beautiful Sonoma Valley landscape, head north on Highway 101.