Boston Area Vacation Rental Manager Delivers Better Service

Liann DiMare started iTrip® North Shore in March 2018, after experiencing iTrip’s management program in action. During that time, Liann and her husband had flipped homes and invested in a short-term rental that was underperforming. After learning about iTrip, they listed their condo. The rest is history. Read more about this Boston area vacation rental manager.

“We purchased a condo-hotel unit in Treasure Island, Florida, and felt that the condo could do better,” explained Liann. “Then we moved our unit to iTrip St. Petersburg Beaches, and our unit’s performance took off! We were so impressed that I called iTrip to inquire about buying a franchise location where we live in Boston’s North Shore.”

Boston Area Vacation Rental Manager Sets a New Standard

Today, Liann owns and manages iTrip North Shore, which serves Gloucester, Ipswich, Newbury, Newburyport, Rockport, Salem and Salisbury in Massachusetts, as well as New Hampshire’s seacoast and ski country regions.

The company offers a full-service program that oversees the entire short-term rental process. iTrip North Shore handles everything from preparing and listing a home, to creating a great guest experience and keeping the home in better condition versus long-term renting. The team also manages revenue management, distribution and marketing, and cleaning and maintenance.

“I love helping homeowners take their properties from concept to cash,” said Liann. “We help them from design, furnishing, listing and then booking. It’s so fun when a property is first listed – and that first booking. It’s like yay! People like my place!”

Short-term Rental Management Secrets in Boston’s North Shore

Maximizing a short-term rental’s potential is half art and half science — where market savvy meets insightful prediction. Liann focuses on anticipating and adapting to shifts in the marketplace. This helps iTrip North Shore’s properties outperform the market, with higher rates and higher occupancy. Plus, iTrip continues to improve their in-house property management and business operations to always improve the owner’s experience.

“Part of the iTrip secret sauce is our properties are more visible by being listed on so many channels, thus creating higher conversion rates, which means more bookings,” said Liann. “The other part is our team deeply cares about each home and each guest. We provide quality care to our homeowners, homes and guests. It’s a partnership.”

Over the years, the short-term rental industry has seen one roller coaster ride. A global pandemic forced travel restrictions, but travel rebounded. Now, short-term and vacation rentals continue to gain popularity, as they offer more flexibility and privacy than traditional hotels. Others have taken notice as well because there are more than 1.2 million listings in the U.S. alone.

“Our greatest success is helping our owners succeed even during tumultuous market conditions,” shared Liann. “We also love helping guests discover quirky events and activities. When a guest books, we help them find local gems – like the cardboard boat race in Beverly and Colonial Ways in Marblehead. Most locals don’t even know about these!”

Five-Star Hospitality Builds Trust and Nurtures Relationships

This personal care can’t be found with other short-term rental managers in Boston’s North Shore region. Many mom-and-pop companies have been bought by large corporations that don’t have the resources to offer hands-on care. With iTrip North Shore, each home is cared for by Liann and her team, who live in and love the area. This is the legacy that Liann and her husband want to leave behind. It’s about generating income for owners and contributing to the local economy through tourism and hospitality.

“Both Boston’s North Shore region and New Hampshire are amazing places to live and visit. Boston’s North Shore is so rich in history — the birthplace of the US Navy, US Coast Guard and US National Guard,” Liann said. “The area offers both culture with tons of green spaces interwoven throughout. Visitors can enjoy a play or concert and be five minutes from a lovely stroll in the woods. They can drive to the beach or mountains. I don’t know many places that give travelers so many options.”

Experience Matters

Prior to becoming an iTrip property manager, Liann had a successful career in business strategies for large corporations. She celebrated her fifth iTrip business anniversary milestone in 2023 and looks forward to more years of serving the community as a short-term rental manager.

“The winding paths of life are how the universe helps you arrive in the right place at the right time,” shared Liann. “We understand first-hand how it feels to own a short-term rental property. Owners should never wonder how a rental property is performing or be surprised by an unexpected maintenance bill. Our team offers transparency, trust and better care. It’s an honor to serve our communities in Massachusetts and New Hampshire.

Learn about listing a rental property with iTrip North Shore.

Want to visit? View vacation rentals in Boston’s North Shore Region and New Hampshire’s North Region.