About iTrip® Annapolis

iTrip Annapolis is owned and operated by Jennifer and Sean Degnan. They serve vacation rental homeowners and guests in Annapolis, Kent Island and St. Michaels.

After meeting Sean and completing her finance degree at Georgetown University, Jennifer returned to Sean’s hometown of Chicago and fell in love with the city's energy. She excelled in account management at an advertising agency covering Fortune 500 companies before transitioning to a prestigious advertising sales position at Nickelodeon. For the last decade, she has since relocated to Annapolis, the city of her dreams. Today, Jennifer keeps a hand in marketing and sales while raising their three children.

After graduating with a degree in government from Georgetown University, Sean realized his love of sales, first in the technology industry and then in the financial services industry. For the last 15 years, Sean built a successful career in upstate New York, Pennsylvania and the Mid-Atlantic. He has established strong relationships with local financial advisors, helping them build and preserve long-term wealth and comfortable retirements. Sean excels at presenting ideas to individuals and large groups, and loves the prospect of building these same relationships with real estate professionals, property owners and visiting guests.

Connect with us today! Let iTrip Annapolis help manage your rental or find your home away from home.

About iTrip
iTrip was started in 2008 by vacation rental owners for vacation rental owners. The company has since grown into one of the top property management leaders in North America. Each iTrip destination is managed by a local team, available 24/7, who lives in the area. This combined with state-of-the-art systems and proven processes enables iTrip to provide boutique-level services backed by a national brand to all our short-term rental owners and guests.