Woodside, CA

As its name implies, Woodside is a lush, verdant small town located between San Francisco and San Jose. Woodside is one of the nation’s most upscale towns to live in and is known for its abundance of equestrian centers and natural areas with scenic trails. At Wunderlich County Park, residents have access to open meadows, hiking and biking trails, and stables. You’ll also be able to see the giant redwood trees Northern California is known for. Horseback riding and bicycling are a major part of the local culture. Many residents keep horses on their property, and the town maintains a network of horse trails for everyone to enjoy.

You’ll find locals cycling along roads like King’s Mountains Road or participating in bicycle races like the Tour of California. When you secure your rental in Woodside, you’ll also probably see a celebrity or a Silicon Valley entrepreneur at the town’s tiny commercial center featuring several upscale eateries and bars. Woodside is purposely secluded, so if you want more variety, you will have to take a short drive to neighboring towns. Woodside is convenient to several major destinations including Stanford University, Silicon Valley, and San Francisco.