Why This Is More Than A Random Short Term Rental

Hands down, the easiest thing to do would have been to take a few pictures, make a quick profile on a short term rental website, sat back and let people come and go while collecting some cash.

However, that’s just not my style. I don’t like doing anything less than 110%. If I’m going to do a project, I’m all in. But beyond that, and more importantly, I genuinely wanted to share this cottage—and the experience of being on the island—with people. I wanted other people to have memories like I do. I wanted other people to be able to think of Great Diamond Island and consider it one of their favorite places on Earth.

I’m a really lucky guy. I never debate that. The Woodbury Cottage has been in my family for three generations. My maternal grandfather bought the house—along with the two next door—when my mom was growing up. Ever since then, being “on the island” has a big part of my family life. I remember summers as a kid when I didn’t ride in a car from the last day of school in June until the day before school started in September. In this crazy and chaotic world full of rapidly evolving technology, I truly value that.

Since it isn’t possible to just pick up, move to the island for the summer and pretend that cars don’t exist at this point in life, I wanted to share the island with whoever wanted experience it and spend time there. This really came from a place of feeling so grateful for what I have that I wanted to share it as much as possible. So, about two and a half years ago, my husband and I made a pact to give it all we’ve got.  He’s got the design eye and I have the logistics eye—a perfect meeting of art and commerce.

Ever since then we’ve been obsessing over every detail. He’s worked tirelessly on making the space as beautiful and functional as possible. I’ve been working on making it easy for people to get to the island and make their stay as effortless as possible. Trust me, you forget one thing you need and it’s a six hour turn around before you can get into town, to the store and back on the ferry island-bound.

There’s a lot that a hotel can offer but we are working really hard to capitalize on what a hotel CAN’T offer and encapsulate it for people to enjoy. There is a reason that the short-term rental industry is on fire and we’re giving it all we’ve got to make sure it’s as special as possible for our guests.

So this is our story. This is how we’re trying to build a unique (I hate to use one of the most over used terms in the vacation rental industry, but there you have it) experience for people. Vacation time is so sacred. How often can you really get your favorite people in one place for a long weekend let alone a week? We are trying to transport people into an experience where it’s as easy and impactful as possible to enjoy time with people that mean the most to them.

So I hope you follow along. I’d love to hear all the feedback you’ve got! Email me, Facebook me, Tweet me, Instagram me…..you know the drill!

Jason