About iTrip Boston and South Shore

Meet iTrip® Boston and South Shore

Jim and Jessica Wood, a husband-and-wife team, own and manage iTrip Boston and South Shore. Together they work with short-term vacation property owners and their guests to offer world-class services through a proven property management program in Boston, Plymouth, and the surrounding areas and coastal communities.

With Jim’s background in financial services and accounting and Jessica’s experience in healthcare sales, they enjoy developing personal relationships with people. The team is well equipped with skills and experiences to help maximize property owner investments, while providing top-level service to guests. As iTrip rental property managers, they are enthusiastic about promoting in an area they know and love.

Jim and Jessica grew up in Marlborough, Massachusetts, and have lived in the state their entire lives. They played sports through high school and college, and have a passion for hosting and hospitality -- especially entertaining during any New England sports game. Their knowledge and pride for the Boston area will have guests talking about their iTrip Boston and South Shore experience for years to come. Plus, Jim and Jessica treat their clients’ properties like their own and guests like their family!

Connect with iTrip Boston and South Shore today! iTrip Boston and South Shore will provide the personal service your home and guests deserve.