National vacation rental pros buy historic seaside inn in Stonington

Two leaders in the national vacation rental industry have purchased a historic Stonington inn as part of their growing portfolio of inns and rental properties in the United States and beyond.

Clifford O’Sullivan LLC purchased Inn on the Harbor, at 45 Main St., from Mattea LLC for $1.58 million.

Dana Moos of Swan Agency Real Estate brokered the deal.

Courtesy / Inn on the port

An old postcard shows the structures of Inn on the Harbor as they were originally used.

The two partners are Billy O’Sullivan and Clifford Johnson. O’Sullivan has over 20 years of vacation rental and hospitality experience. His career includes time with one of the world’s largest property management companies, Property Management Inc. Most recently, O’Sullivan served as CEO of ALTIDO, a London-based property management company established in 2019. He developed ALTIDO until its merger this year with DoveVivo. , the largest coliving company in Europe, according to its website.

Johnson is a co-founder of vacation rental management company Vacasa who left in 2018 and is now an executive at

“Cliff and I always said we wanted to do something together and be family-style and cool, but stay in the hospitality space,” O’Sullivan said.

Fishermen village

The sellers, Dana Durst and her husband Jay Brown, had owned Inn on the Harbor since 2016.

The hostel comprises four small historic buildings on the narrow main street of the fishing village, overlooking the harbour. Features include antique counter tops, wide plank flooring and a large rear deck supported by stilts.

Courtesy / Inn on the port

Inn on the Harbor is an eclectic collection of structures featuring a large back deck supported by stilts.

In the back, there is a maze of wooden stairs, small terraces on the upper floor and cedar shingles. Nine oceanfront rooms on two floors have double doors or bay windows. Four bedrooms overlook Main Street. The chimneys of several rooms are clad in brick and marble. Furnishings include antiques such as box springs, bedside tables, rugs and trunks. One of the buildings, a former hair salon, has an original sheet metal ceiling. The rooms are named after windjammers, such as Stephen Taber and Mary Day, who cruise the Deer Island thoroughfare. Modern amenities include Wi-Fi and a flat-screen TV. These features caught the attention of buyers.

“I love this place,” O’Sullivan said.

The beginnings of hospitality

O’Sullivan said he’s been in the vacation rental business “by accident” since he was a teenager renting his apartment in California, where he became a Hollywood television director and producer at a young age.

“A lot of times I would be on site or off,” he said. “I decided I was going to stick up a flyer of my condo and see if anyone wanted to rent my spot.”

It was in the 1990s, before the creation of Airbnb.

“People would call, I would give them my keys and they would give me a check,” he said. “It was an enchanting start to my hospitality career from the start.”

In one form or another, he’s been in the short-term rental business ever since, first with his own rentals in places like Hawaii. Property Management Inc. eventually contacted him and asked him to design a franchise program for people interested in running short-term rental businesses. He worked with the company for a few years, helping them open offices in several locations before moving to the UK to develop and market ALTIDO.

Change speed

But he likes to get around a lot, so he switched gears to start a business called Ohana Inns with Johnson.

Partners now have vacation rentals and hostels in seven states and overseas partnerships in Costa Rica, Morocco, Egypt, Chile and Scotland.

But they wanted to develop a different business model for their hostels.

“Cliff and I have both seen too many housekeeping and maintenance people pushed aside when times are tough or slow,” he said.

The idea was to reposition seasonal hostels as year-round properties, with rooms available for tourists during peak season. During the off season, rooms could be rented out on a short-term basis to people such as traveling nurses and students. The properties would also house people who worked in seasonal businesses and employ them out of season, providing them with a year-round income.

gnarled cliffs

The partners identified Maine as a good business prospect through a friend who lived in Maine and encouraged them to visit Acadia National Park. O’Sullivan and his wife are ultra-runners who run 200-mile races.

“He kept saying, ‘You’ve never done these hikes in Acadie,'” O’Sullivan recalls. “‘There are these gnarly cliffs and killer gravel roads to ride your bike on.'”

As a result of this visit, the partners spotted a listing for the Open Hearth Inn in Trenton. After checking it out, they thought it was a worthwhile investment, especially since it was located on the only road to Mount Desert Island and Acadia, thus having a captive audience.

“It was a natural place to say, ‘Hey, if business isn’t good enough and we can’t find staff and we’re stuck managing it, that’s no problem,'” a- he declared.

The partners purchased the Open Hearth in 2021 and developed it with the new business model in mind. They kept it open year-round by renting rooms to traveling nurses, Atlantic College students, and others.

“We were able to make a lot of money over the winter and keep our staff paid,” he said.

They also installed self-check-in technology and implemented an approach that allows guests to use the hostel more like a home.

“It removes the reception and the door from the innkeepers’ section, making everything a common area,” he described. “We make all the space for people to find each other. Make yourself a bowl of oatmeal, then use the hot tub on the back deck. Kind of like a community vibe where you have your own space but you also have real common space, but it’s not a lame, sterile hotel lobby.”


In 2021, as he reopened the Open Hearth, O’Sullivan lived for several months in his 19-foot trailer, parked by a creek in the backyard.

“My wife and I feel more comfortable being nomads,” he said. “We are blocking out some time at our properties so we can go back and reconnect with them and check in. We like to be flexible, free and free. We’ve been in Hawaii for a long time, but Maine is just as much our home now as it is anywhere else.

The partners plan to implement the Open Hearth model at Inn on the Harbor in Stonington.

Courtesy / Inn on the port

The Inn on the Harbor in Stonington comprises four small historic buildings on the narrow main street of the fishing village.

“We just want to think about it,” O’Sullivan said. “We want to at least get to know and work with people and provide a really cool experience.”

This includes discussions with the local community.

“We go through this whole process of learning what Stonington wants,” he said. “There are so many things we can do with the Inn on the Harbor. There is a coffee area and the terrace. They are incredible and inspiring spaces. We want it to be really fun and for people to be excited to come back.

Financing for both properties was secured by mortgages with First National Bank.

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