About

About The Charlotte Inn

A Place Apart. A Past Preserved.

Nestled on a quiet, tree-lined street in Edgartown, The Charlotte Inn is a world away from the everyday. Step inside and you are transported—to a time of quiet elegance, graceful hospitality, and refined simplicity. This is not just a place to stay. It is a place to linger.

With its ivy-covered brick paths, antique-filled rooms, and artfully curated details, the Inn offers a setting as timeless as it is inviting. Guests often speak of feeling as though they have stepped into another era—one where the pace is slower, the welcome warmer, and every detail is meant to be savored.

A Legacy Preserved Through Generations

The Charlotte Inn is more than a destination—it is part of the island’s living history. Built in 1866 by whaling captain Samuel Osborn Jr., the grand home was designed to reflect Edgartown’s seafaring prosperity and social stature.

Over the next century, it would serve as a family home, a grocery store, and, beginning in 1934, a modest island inn founded by Charlotte Pent—a woman known for her hospitality and unshakable charm. The inn changed hands several times, eventually falling into disrepair.

But in 1971, the property caught the eye of Gery Conover. Alongside his wife Paula, Gery began a careful, loving restoration of the home, reviving its elegance and creating the refined, one-of-a-kind experience that defines The Charlotte Inn today.

Together with their golden retrievers, Morgan and Bentley, the Conovers continue to own and operate the Inn—welcoming generations of guests who return year after year for the quiet magic it offers.

The Charlotte Inn Through the Years

1866

A Grand Seafaring Home

Captain Samuel Osborn Jr., a prominent whaling ship owner and businessman, builds a stately three-story residence for his wife Zoraida and their sons. The home quickly becomes a centerpiece of Edgartown society—designed to impress with its architectural presence and to reflect the prosperity of a family deeply tied to Martha’s Vineyard’s maritime past.

1900

A Bustling Island Market

After the Osborns, the home is purchased by Manuel Silva Jr., a former sailor turned shopkeeper. He transforms the first floor into one of the island’s most modern grocery stores, a hub of everyday life for Edgartown residents. With its red Victorian porch and prominent signage, the building evolves from private home to community gathering place.

1943

A New Vision by Charlotte Pent

Charlotte Pent, with deep island roots and an eye for hospitality, converts the property into an elegant guesthouse bearing her name. She replaces the market with refined parlors and guest rooms, transforming the building into a genteel inn known for its grace and charm. Despite the challenges of the Great Depression, her venture thrives and serves travelers for two decades.

1955–1970s

A Period of Decline

Following Charlotte Pent’s retirement, the inn changes hands and gradually loses its luster. The once-elegant home falls into disrepair, its original beauty obscured by time and neglect. For years, it waits quietly—its next chapter uncertain but its bones still full of promise.

1971

A Loving Restoration Begins

Newly arrived on the island, Gery Conover sees potential in the forgotten inn and purchases the property. With the help of his wife Paula, Gery embarks on a decades-long labor of love, restoring the house with period-appropriate materials, antiques, and an unmatched eye for detail. The inn slowly regains—and surpasses—its former glory.

1992

A Mark of Distinction

The Charlotte Inn is recognized by Relais & Châteaux, joining a prestigious fellowship of boutique hotels known for their exceptional charm, service, and culinary excellence. The honor reflects the Conovers’ meticulous work and cements the Inn’s place as one of the world’s truly special escapes.

2018

A Hallmark Debut

As Seen on Hallmark: A Godwink Christmas at The Charlotte Inn

The Charlotte Inn and its beloved owners, Gery and Paula Conover, were featured in A Godwink Christmas—a Hallmark Movies & Mysteries film that told the true story of how the couple met over 30 years ago. The Inn itself played a charming supporting role.

Present Day

An Enduring Island Icon

Now a beloved retreat for travelers from across the globe, The Charlotte Inn remains privately owned and operated by the Conover family, with their golden retrievers Morgan and Bentley often nearby. Every stay offers the same warmth, elegance, and attention to detail that have made the Inn a treasured part of Edgartown’s past—and present.

The Pleasure is in the Details

At The Charlotte Inn, luxury is expressed through quiet moments and thoughtful touches. Here are just a few of the experiences that await:

Morning coffee or tea in the garden courtyard
A glass of sherry by the library fireplace
The Edgartown Art Gallery, featuring original works by regional and international artists
Candlelit dinners at The Terrace, our fine dining restaurant

Crisp linens, antique furnishings, and fresh flowers in every room
Personal concierge service for a seamless stay
Bicycles for exploring Edgartown and the island’s scenic trails
A curated library of books and fine magazines
Gentle hospitality that never intrudes, but always attends

Come experience it for yourself.

The Charlotte Inn is not simply a place to stay—it is a place to remember.