By Ginger DeShaney

The Boston Bailey B&B is the home of American history. Or at least a home of American history.

The Boston Bailey, a 5-star registered short-term rental property at 101 P Street, is owned by Bill and Maureen Bailey.

One suite is called “One By Land,” another is called “Two If by Sea,” and the third is “The Paul Revere Suite.” There’s also the “Tea Party Welcome Room.”

The history brings people in, said Bill, a history buff who noted the house’s foundation dates to 1832-33 and the oldest frame goes back to 1875. 

Bill was always reading “dry, old” history books even though he already knew the endings, he joked. “… you look at the virtue of the people back then when they were designing this country, developing this country,” said Bill, who attached himself to those principles and virtues. 

So it was important for Bill to bring history into the suites. “It starts the conversation.”

When the Baileys bought the house 30 years ago, it hadn’t been well taken care of, so they renovated. “It was a nice project,” Bill said. “Like any old house, you really have to maintain the essence of it.”

The stunning entrance to the house stops visitors in their tracks. A large mural depicting the Boston Tea Party and a lighthouse graces the wall up the staircase. “I wanted to do something different going up these stairs,” said Bill, who with MassArt graduate Kamali Thornell created the mural decades ago.

When Bill and Maureen became empty-nesters, they needed to make a decision regarding their 12-room house. “The trends were tough. If we would have moved, we knew this house would have been demolished,” Bill said. “We were like, OK, we need to preserve this … I didn’t want to convert it to a two-family. I wanted to keep the essence of the house.” 

People told them about short-term rental platforms. “We did some research on it and here we are,” Bill said. They opened in 2018.

“It’s exciting for us,” he said. “We’re happy to be doing it. It allows us to keep an old house as an old house in Southie.

“I’m trying to capture history for as long as I can here,” added Bill, who is vice president of the City Point Neighborhood Association.

Bill and Maureen both work full time. Bill is a resident engineer with City Point Partners and Maureen works at Boston College. But when they get closer to retirement, they have plans to turn the Boston Bailey into a full-time Irish style B&B, complete with breakfast and an eating area. (They currently offer a continental breakfast.)

The three newly remodeled luxury suites, each with its own bathroom and keyless entry, offer historic charm and modern conveniences, including workspaces and Wi-Fi.

Bill is a fourth-generation South Bostonian. He hosts an Irish music radio program from 4-7 p.m. every Saturday on WROL called “Bailey Ceili.” 

“It’s a lot of fun when you find your lineage,” he said. 

“This is why it’s so important that you maintain your history in the community during development,” said Bill, who works with developers to maintain the lineage of neighborhoods. 

“You don’t want to lose how the neighborhood evolved … just to maintain its history and where we are,” added Bill, who also owned an Irish Pub, the Bailey, for five years.

Bill and Maureen, who owned Pleasure Bay Travel for about five years, provide their guests with a guide to attractions. The top destinations? The Freedom Trail, Regina’s, and Mike’s Pastry. Fenway Park is also right up there. 

Guests also take advantage of Southie’s beaches and Castle Island, Bill said, noting that it’s nice to have a historical house just a 20-minute walk to historic Fort Independence. 

The Boston Bailey shut down for a while during the COVID-19 pandemic. But things are starting to come back, Bill said, noting he’s seeing more traffic to the website and more bookings.

Word of mouth, stellar reviews, friendly owners, and competitive pricing draw guests and create repeat customers.

Before COVID, the Boston Bailey was fully booked and attracted a lot of convention-goers during the week and pre- and post-cruise guests on the weekends.

A lot of the Baileys’ neighbors are young people, so they also get a lot of parents who visit their children. 

They’ve had guests from all over the world.

The Baileys follow strict COVID guidelines. In October, they started booking again at 25 percent capacity. There’s a two-night minimum stay for guests and a day in between bookings so Bill and Maureen can deep clean the suites.

The Baileys live on the bottom floor of the house so Bill will chat briefly with the guests if he sees them in the hallway and is always ready to answer questions. “It’s nice to talk and experience other people’s viewpoints,” Bill said, noting they’ve had wonderful guests. “It’s nice to have that communication with people, just nice to know how other people are, how they’re doing, especially post-COVID.

“It reinforces the fact that there are great people out there.”

And that’s just part of the Boston Bailey’s history.


Bill and Maureen Bailey