Vacation rentals in Woodside

Woodside is a small, affluent incorporated town in San Mateo County, California, tucked into the western foothills of the Santa Cruz Mountains in the San Francisco Bay Area. The community preserves a rural, equestrian-oriented character with scenic hills, open space, and a quaint, low-key downtown, making it a tranquil base for visitors. It's conveniently close to Menlo Park and Portola Valley, with easy access to Peninsula sights, outdoor trails, and a variety of dining and shopping options.