About iTrip Pittsburgh

Meet the Owner

Jeremiah Dodrill brings over two decades of senior leadership experience in financial management and operations to iTrip Pittsburgh. With a proven track record of driving financial success and operational excellence, Jeremiah is dedicated to providing exceptional vacation rental experiences for property owners and guests throughout the Steel City.

Originally from Oregon, Jeremiah relocated to Pittsburgh in 2024 to be closer to his youngest daughter, embracing the city’s vibrant culture, rich history, and strong sense of community. As a short-term rental owner himself, with two properties in Oregon successfully managed by iTrip, Jeremiah was drawn to the iTrip franchise for its proven model and commitment to excellence. His career includes executive roles in healthcare, such as Chief Financial Officer at Pittsburgh Mercy Health System and Southern Coos Hospital & Health Center, where he led multimillion-dollar contract negotiations, implemented innovative financial systems, and drove strategic initiatives that enhanced profitability and efficiency. These skills now fuel his commitment to delivering top-tier property management services.

In his free time, Jeremiah cherishes moments with his three children, engaging in outdoor recreational activities like camping, hunting, and fishing, and enjoying live music events. As a newer Pittsburgh resident, he’s an avid sports enthusiast, cheering for exciting games while exploring the city’s dynamic sports culture. Jeremiah is passionate about showcasing Pittsburgh as a premier travel destination and helping property owners succeed in the short-term rental market.

About iTrip

iTrip is a short-term and vacation rental management company with local property management companies based in destinations from coast to coast. Created by short-term rental property owners, for short-term rental property owners, the company began in 2008 to bring the best of traditional rental management paired with the power of an international marketing machine.

Today, iTrip manages vacation and short-term rental properties in more than 100 destinations across North America, including Canada. This translates to increased revenues and conversion rates 5 times the industry average. On average, our owners see an increase of 25% revenue, versus self-managing, after listing with iTrip.

Contact iTrip Pittsburgh to meet Jeremiah and list your property.