Gerry and Paula Conover

Gery and Paula Conover, Innkeepers

The Charlotte Inn’s refined legacy

The Charlotte Inn in Edgartown revisits the grand and glorious lifestyle of Edwardian-era England. The transformation of the original 1864 house and property – including its meticulously restored buildings, manicured gardens and grounds, and impressive collections of art, antiques, and period furnishings – has been a longtime labor of love.

Now entering their fifth decade as owners and innkeepers on the island of Martha’s Vineyard, Gery and Paula Conover have earned countless accolades and awards for the inn’s gracious hospitality, elegant luxury accommodations, and devoted attention to detail and comfort.

Visit our Accolades and Awards page.

A storied past

From the outset, the imposing three-story house on South Summer Street was one of Edgartown’s most handsome homes, built to shelter, impress, and capture the grandeur of its time. Yet it went through three distinct lives before it became today’s Charlotte Inn. Its story begins when Samuel Osborn Jr., a nineteenth-century whaling ship owner, built the house for his wife, Zoraida, and their two sons.

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Charlotte Inn memorabilia

Osborn (whose family built the Osborn Wharf, now the site of the Edgartown Yacht Club) joined the whaling business at a time when most of that industry had already moved to New Bedford. And in 1862, Osborn’s ship, the Ocmulgee, was the first vessel burned and sunk by the Confederate privateer Alabama during Civil War raids that eventually destroyed sixty-nine vessels and inflicted a devastating blow on the North’s shipping trade. But Osborn was nevertheless successful in his endeavors. By the time the house was finished in January 1866, it was a hub of the town’s sparkling social scene, befitting his status as a political and business leader.

Home to a grocery store


South Summer Street grocery store, early 1900s

The house remained in the Osborn family until the early 1900s, when another man of the sea, Manuel Silva Jr., purchased it. At age thirteen, Silva, the oldest son of a Portuguese immigrant, had shipped out as a cabin boy, but upon retiring from his seafaring life he went into the grocery business. He operated a grocery store in Edgartown for twenty-five years, moving it several times before winding up in the old Osborn place on South Summer Street. There he erected a prominent sign on the building’s distinctive red Victorian porch. His store was considered the most up-to-date shopping place in town.

In 1922, Silva sold the business to Charlotte and Philip Pent, a couple from Staten Island with deep Vineyard roots. Pent was the son of Samuel Pent, the first volunteer soldier from Edgartown when the Civil War broke out. Eighty-three years earlier, Pent’s grandfather had himself founded the grocery that Manuel Silva would later operate. Now the Pents retrieved ownership of the store and their Vineyard lives. However, within a few years, the changing economy began to affect the Summer Street grocery. Chain stores came to the Vineyard, the Great Depression hit the country, and the Pents saw their business dwindle. They began to explore other options.

Welcoming visitors

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Charlotte Pent

The year 1934 was not an easy time to change course, especially setting up a new inn for tourists on an island seven miles off the coast of Massachusetts. Yet Charlotte Pent met the skepticism with “a familiar twinkle in her eye,” according to the Vineyard Gazette. Carpenters pulled off the ornate red veranda and built today’s elegant Greek revival–style entrance. The first-floor store, with its shelving and stacked groceries, was revamped into a spacious parlor and a large dining room, with eleven guest rooms and five baths upstairs. “Everywhere great care has been taken to preserve the simple dignity and beauty which goes naturally with the old house,” the Gazette story reported. Charlotte Pent named the inn after herself, and the successful transformation kept the inn operating for some twenty years.

By 1955, Charlotte Pent, then a widow, sold the property. It changed hands twice more, and the buildings and grounds grew increasingly unkempt. Its sad decline was halted dramatically in the spring of 1972, when Gery Conover, who had recently moved to the island, recognized its potential and bought the old Osborn property. Gery’s subsequent years of meticulous restoration, renovation, and improvement have brought The Charlotte Inn to the attention of discerning hotel guests the world over.

Behind the Times on Purpose left

Behind the times on purpose

Behind the Times on Purpose

Behind the Times on Purpose is an elegantly designed coffee table book showcasing the manicured gardens and grounds, the meticulously restored buildings, and the extensive collections of art and antiques housed within The Charlotte Inn. Published by Vineyard Stories, with photographs by Nina Bramhall, this book is a lovely reminder of your visit to The Charlotte Inn, the perfect accompaniment to an inn gift certificate, or a source of endless inspiration for your own home renovation. 

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