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A look inside Cape Cod’s newest five-star hotel

A Florida attorney and his wife transformed a rundown inn into a nationally lauded property

A guest room at the Chatham Inn.Handout

CHATHAM — When the Chatham Inn received its five-star rating from Forbes Magazine in April, there was a bit of confusion, even among the New Englanders who descend upon Cape Cod each summer.

Isn’t it called Chatham Bars Inn?

The confusion was understandable. Chatham Bars Inn has been around since 1914 and has more than 200 rooms. The Chatham Inn arrived in 2015 and has just 18 rooms. Now the difference between the two is more than the word “Bars.” For those keeping count, the Chatham Inn has five stars, Chatham Bars has four.

What’s most remarkable about the ascent of the Chatham Inn from frumpy to fashionable is how quickly it happened. Less than 10 years ago it was known as the Cranberry Inn. At the time, it was a traditional bed and breakfast, complete with dust ruffles, floral swag curtains, oval braided rugs, and plenty of doilies.


But underneath the doilies and floral accent pillows was a landmark structure. The building is the oldest continually operated inn on Cape Cod. It was built in 1830 and changed hands, and names, multiple times.

“I don’t think it had seen a new coat of paint since the Reagan administration,” said Chatham Inn owner Jeff Ippoliti. “But we walked in, and my wife, Kayla, said, ‘This is it.’ It took her about five seconds. I looked around and said, ‘Are you sure?’ The linoleum floors were peeling up, and the plastic shower liners may have been white at one point, but they weren’t anymore.”

The couple placed an offer on the Cranberry Inn after seeing it in 2013 but lost out to another buyer. When it came back on the market two years later, their bid was accepted, and they launched a series of extensive renovations. Ippolito declined to say how much he paid for the inn but said the cost of renovations has far exceeded the price of the property.


The lobby of the Chatham Inn. The property received a five-star rating from Forbes Magazine in April.Handout

“It’s tough when you’re dealing with a 200-year-old building,” he said. “We were also working through this labyrinth to comply with the rules of a historic building in a historic district. So making changes is a challenge.”

The other challenge they faced was learning to run an inn. Neither had done it before. Ippoliti is an attorney who practices law in Florida with his brother. His only other foray into the hospitality business was owning two restaurants in Syracuse, N.Y. But both he and his wife are avid travelers and always fantasized about opening an inn. Specifically an inn on Cape Cod. When Ippoliti decided to step back from working full time, they made the jump.

“I would come with my cousins and extended family and stay in a tiny little cottage in South Yarmouth,” he said. “So I have these fantastic memories of Cape Cod growing up and I have loved it here my whole life. I was born in July and I’ve spent all of my birthdays here, all the way back to my first. My wife had never been to the Cape. When we visited, she fell in love with it.”

Because their progression to innkeepers didn’t follow the usual trajectory, there was some confusion in Chatham about why an attorney from Florida (with an impressive vintage car collection, no less) wanted to make such a radical life change.


“At our first selectmen’s meeting, they actually said, ‘How did a guy like you from Florida, with a last name like yours, end up on the Cape?,’” he recalled. “I just thought to myself ‘Did you actually just say that?’ I was a little shocked.”

With the purchase and approvals in place, they began renovations with a very specific goal. They weren’t looking for five stars from Forbes, they wanted to be part of the Relais & Châteaux hotel and restaurant group.

The Chatham Inn was transformed from shabby to chic. This year it was recognized as an extraordinary luxury property by Forbes.Handout

For those who don’t follow luxury hospitality, Relais & Châteaux is an association of nearly 600 individually owned hotels and restaurants. Becoming a part of the Relais & Châteaux group is the luxury hotel equivalent of earning the Good Housekeeping Seal of Approval or an A+ from the Better Business Bureau, except much, much fancier. The organization looks at 300 different aspects of each property and then makes its decision based on criteria such as the uniqueness of the property or the level of service. A hotel or restaurant must apply to be a member. Jeff and Kayla Ippoliti applied four times before finally being accepted in 2019.

The advantage to being a member is not only status. Some travelers specifically look for Relais & Châteaux hotels when planning accommodations. There are 14 Relais & Châteaux hotels and restaurants in New England, including Blantyre in Lenox and Twin Farms in Barnard, Vt. The drive to become a part of the organization was based on the couple’s own experiences while staying at hotels.


The dining room at Curvée, the restaurant at the Chatham Inn.Handout

In addition to the inn, there is also a fine dining restaurant called Cuvée. It offers four- and seven-course tasting menus with options such as ambrosia foie gras torchon and halibut in porcini crumb. Most nights you can find Jeff and Kayla delivering entrees to customers alongside servers.

The inn is open year-round, and the Ippolitis plan to stick it out through Cape winters rather than retreating to Florida when the weather turns.

“We built a hotel and a restaurant that we would want to come to,” he said. “Fortunately other people like it as well. We love this place, and most of the rooms have fireplaces, so why wouldn’t we want to be here?”

359 Main St., Chatham, 508-945-9232, Prices range from $350 to $1,000 nightly depending on season and availability.

Christopher Muther can be reached at Follow him @Chris_Muther and Instagram @chris_muther.