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Updated: June 20, 2022

National vacation rental pros buy historic seaside Stonington inn

person with flagpole on lawn Courtesy / Ohana Inns Billy O’Sullivan is part of a partnership that bought Trenton’s Open Hearth Inn, seen here, and Stonington’s Inn on the Harbor to extend the seasonal model to year-round rentals.
By Laurie Schreiber

Two leaders in the national vacation rental industry bought a historic Stonington inn as part of their growing portfolio of inn and rental properties in the U.S. and beyond.

Clifford O'Sullivan LLC bought 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.

old buildings
Courtesy / Inn on the Harbor
An old postcard shows Inn on the Harbor’s structures 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. More recently, O’Sullivan was CEO of London-based ALTIDO, a property management company established in 2019. He grew ALTIDO to its merger this year with DoveVivo, the largest co-living company in Europe, according to its website.

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

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

Fishing village

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

The inn includes four small historic buildings on the fishing village’s narrow Main Street, overlooking the harbor. Features include antique counters, wide-plank flooring and a large back deck supported by pilings. 

cedar shingled buildings dock water
Courtesy / Inn on the Harbor
Inn on the Harbor is an eclectic collection of structures including a large back deck supported by pilings.

Out back, there’s a warren of wooden staircases, small upper-story decks, and cedar shingling. Nine oceanside rooms on two stories have double-doors or picture windows. Four rooms overlook Main Street. Fireplaces in several rooms are faced with brick and marble. Furnishings include antiques such as bedsteads, end tables, rugs, and trunks. One of the buildings, a former barbershop has original tin ceiling. Rooms are named after windjammers, such as Stephen Taber and Mary Day, that sail through the Deer Island thoroughfare. Modern amenities include wifi and flat-screen TVs. Those features caught the buyers’ eyes.

“I love that place,” said O'Sullivan.

Hospitality beginnings

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

“A lot of times I’d be on location or away,” he related. “I decided I was going to paste up a flyer of my condo and see if anyone wanted to rent my place.”

It was the 1990s, before Airbnb was founded.

“People would call, I’d give them my keys and they’d give me a check,” he said. “It was a charmed beginning to my hospitality career from the get-go.”

In one form or another, he’s been in the short-term rental industry ever since, first with his own rentals in places like Hawaii. Property Management Inc. eventually reached out and asked him to design a franchise program for people interested in running short-term rental businesses. He worked with the company a couple of years, helping them to open offices in a number of locations before moving to the United Kingdom to grow and market ALTIDO.

Switching gears

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

The partners now have vacation rentals and inns in seven states and partnerships abroad in Costa Rica, Morocco, Egypt, Chile and Scotland. 

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

“Cliff and I have both seen too many  housekeeping and maintenance people get shelved when times are bad or slow,” he said.

The idea was to reposition seasonal inns as year-round properties, with rooms available for tourists during peak season. During the off-season, rooms could be rented short-term to people such as traveling nurses and college students. The properties would also house people who worked at seasonal businesses and would employ them during the off-season, thus ensuring they had a year-round income.

Gnarly 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 do 200-mile races. 

“He kept saying, ‘You guys have never gone on these hikes in Acadia,’” O’Sullivan recalled. “‘There are these gnarly cliffs and killer gravel roads to ride your bike on.’”

As a result of that visit, the partners spotted a listing for the Open Hearth Inn in Trenton. After checking it out, they figured it was a worthwhile investment, particularly because it was located on the one road funneling to Mount Desert Island and Acadia, thus having something of a captive audience.

“It was a natural spot to say, ‘Hey, if business isn’t good enough and we can’t find staff and we’re stuck running it, that’s not a problem,’” he said.

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

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

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

“That takes the front desk out and takes the door off from the innkeepers’ section, making everything a common area,” he described. “We make the whole place for people to hang out. 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 hotel lobby that’s lame and sterile.”

Nomads

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

“My wife and I feel most comfortable being nomadic,” he said. “We block out a little bit of time at our properties so we can go back and reconnect with them and check in. We like to be flexible  and footloose and free. We’ve called Hawaii home for a long time, but Maine is just as much home now as anywhere else.”

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

mustard and green small buildings
Courtesy / Inn on the Harbor
Inn on the Harbor, in Stonington, includes four small historic buildings on the fishing village’s narrow Main Street.

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

That includes discussions with the local community.

“We’re going through this whole learning process of what Stonington wants,” he siad. “There’s so much we can do with the Inn on the Harbor. There’s a café space and the deck. Those are some inspiring incredible spaces. We want to make it really fun and have people who are excited about coming back.”

Financing for both properties came through mortgages with First National Bank.

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