Meet the iTrip Vacations Ocean City Team

Meet the iTrip Vacations® Ocean City Team

iTrip Vacations Ocean City is owned and operated by Herb Chisholm and Roger Berwanger. With a focus on local, boutique-level care, they strive to provide personal care to rental owners and guests.

Read more about our full-service property management program in Ocean City.

Herb Chisholm

Herb Chisholm began his real estate career in 1982. He spent his first 10 years with Coldwell Banker, including managing the Severna Park office for three years. Herb then spent 20 years with RE/MAX, and during that time achieved the honor of being named to the RE/MAX Hall of Fame because of the volume of real estate sales achieved. In 2008, he decided to operate his real estate business under his own brokers license and left RE/MAX.

During those years in real estate, Herb decided there was a need to help his owners during the down-market by finding qualified tenants to rent their home until the market rebounded. It was at that time that Herb added residential property management to the services he offered his clients. Over the following 25 years, Herb managed between 50 and 80 homes each year, in addition to continuing to list and sell to buyers and sellers.

In addition to helping buyers and sellers, Herb also dedicated time to his local Board of Realtors serving on several committees, including the Legislative, Community Service and Professional Standard committees. He was also honored by his local Association of Realtors in 1991 as Distinguished Sales Associate of the Year. In addition, Herb served as President of the Anne Arundel County Association of Realtors in 1992 and the Maryland Association of Realtors in different capacities, including the Legislative Committee and RPAC Trustee.

Herb is a Maryland native, and he and his wife, Susan, have four children. He is an avid golfer, loves boating and traveling to the Caribbean Islands with his wife.

Roger Berwanger

Roger Berwanger's career has covered three areas: banking and finance, technology commercialization and serial entrepreneurship.

Roger began in commercial banking. He rose rapidly to become a C-level executive in a NYSE-listed bank holding company. His expertise focused on profit center performance management, corporate planning and investment banking. While there, he was cited as a D&B member of Who's Who in Finance and Industry.

Roger left banking in the late 80s to join SaraTech Finance, a division of the Center for Space and Advanced Technology. He performed as a Program Manager for three NASA-funded IT projects and helped pioneer satellite-based video technology to education and training.

Roger was recruited in the mid-90s by the Bank Advisory Group. He performed as a Senior Financial Advisor and World Bank IT-project bid coach. He advised government Finance Ministries and Fortune 100 firms doing business in the UK, Germany, Austria, Poland, Russia, Ukraine, Kazakhstan and India.

In the late 90s, Roger shifted his focus to small business ownership. He co-owned Grafik Industries Ltd. and Joan Carol Design Group. Later, he founded Accurate Media LLC in 2012. Accurate Media is a HubSpot partner, a member of the Content Marketing Blueprint Community and an Inbound Marketing Consultancy.

Roger and his wife, Judy, acquired Senior Helpers of Annapolis in 2008. The couple operated the Alzheimer's/dementia care franchise until they sold the business in 2013 and relocated to live at the beach permanently.

Roger's education includes an MBA in finance, a B.S. in economics and undergraduate work in mathematics and post-graduate work in econometrics and probability and statistics. He is a licensed Maryland Realtor and a former licensed Maryland real estate appraiser.

Roger is a former sailboat owner, a semi-pro photographer, plays golf poorly and an avid traveler. He and Judy have two sons. The couple spends their spare time at the beach, especially in the late afternoon when crowds are gone and the sun is setting.

Judy Berwanger

Judy Berwanger began her career as an elementary school teacher. She later became an educator and curriculum developer for technology education. Here, she serviced schools and trained teachers to implement technology curriculum in their schools.

Judy later joined Roger as a co-owner at an international tradeshow dealership. She was responsible for business development and overseeing production of custom tradeshow products for government and corporate clients.

Most recently, Judy served as a co-owner of an in-home healthcare business. She was responsible for business development, hiring and training caregivers, and guaranteeing customer satisfaction. She holds a B.S. in education and enjoys book club, cooking, travel and the beach.