Property Management in Boston and South Shore

Short-Term Rental Property Management by iTrip

See what you can earn
Jim and Jessica Wood

By Property Owners
For Property Owners

At iTrip®, we’re all about personalized property management because we get it—we’re property owners, too. Your property is your income, and our location franchisees are invested in your success. Our boutique customer service ensures your questions are answered, your peace of mind is in tact, and your property is expertly maintained. Plus, we partner with dozens of rental services to maximize marketing and keep your property booked.

iTrip® Boston and South Shore has managed vacation rentals in Boston, Plymouth, and the surrounding areas and coastal communities since 2022. Homes include beachfront beauties, pet-friendly accommodations, and luxurious rentals with decks and views.

Guests have everything they need for a memorable stay. Each home comes with comfortable bedding, dining areas, WiFi, full kitchens, and a welcome bag with toiletries and laundry starter. Families and pet owners also enjoy rentals with large fended-in yards perfect for everyone to run and play outside.

Those who list with iTrip Boston and South Shore experience the best short-term rental property management in the area. We are locally owned and operated, so we personally inspect each home and work with homeowners directly. There are no call centers – just great service paired with strategies to ensure the rental maximizes its potential. Plus, we oversee the entire process, from staging and listing the rental to gathering five-star reviews.

Get a free rental revenue analysis today! iTrip Boston and South Shore provides the personal short-term rental property management your home and guests deserve.
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Reasons to List with iTrip

Lower Owner Fees
Keep more of your money, just by listing with iTrip.
Superior Property Marketing
Your property gets maximum exposure on up to 85 international websites.
No Markups on Maintenance
Because you shouldn’t get a $20 bill to change a lightbulb. And with iTrip, you never will.
  • Competitive Management Fees
  • Free Light Maintenance
  • 24/7 Support from Local Property Managers
  • Quick-response Systems that Automatically Send Quotes
  • Free High-quality Photos and Videos
  • Worldwide Marketing and Social Media Efforts
  • Exposure on 80+ International Online Listing Sites
  • Owners' Portal: Online Statements, Bookings, Updated Calendars
  • No Restrictions on Owner Usage

Your Boston and South Shore Property Managers

iTrip® Boston and South Shore
35 Thomas Drive
Marlborough, MA
(617) 744-3390
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!
Let's talk
Reviews and Testimonials from Property Owners
  • It's good to know the people behind the scenes at iTrip take care of your stuff as if it's their own. If you have any indication or thought of having your own extra income with your rental property, I strongly recommend using iTrip.

    - Greg J.
  • To my surprise and financial enjoyment, my property grossed $50,000 in one year. The level was professionalism and financial reporting was second to none.

    - Chris S.
  • With iTrip, I can get my time back, enjoy my family and never miss a call because they're there taking them for me. I feel they look out for my property as much and as well as I could.

    - Francine D.
How to List with iTrip
Step One
Fill out the simple form below with some basic info about you and your property.
Step Two
We'll reach out to gather more details, if necessary, and answer any questions.
Step Three
You'll receive a custom revenue forecast that show exactly how much more you could earn from your property by listing with iTrip®.

Request your personalized revenue forecast to see what you can earn.

Questions? Let's talk.

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(617) 744-3390

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iTrip Boston and South Shore
35 Thomas Drive
Marlborough, MA

Browse All Available Properties in Boston and South Shore
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