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Round Hill History

Originally opened in 1953, Round Hill was conceived by well-connected, Jamaican-born entrepreneur John Pringle, whose mother was a social fixture and owned the former Sunset Lodge Hotel in Montego Bay. The 100-acre peninsula was part of Lord Monson's huge Round Hill Estate, which was first a sugar plantation and later grew coconuts, pimento, and allspice. The peninsular bluff was also home to pineapple groves, which are now represented in the signature logo of this prominent Montego Bay resort

Pringle's vision was to take the 'boutique' concept both onto another level and into a new domain. The plan comprised the design and development of a luxury cottage complex in Montego Bay, Jamaica – an early boutique hotel – which, based on John's own revolutionary business model, would offer those who purchased a cottage a share in hotel profits. In other words, he had the idea of creating a Montego Bay resort that would appeal to the very rich who wanted to have a cottage in the West Indies without the problem of absentee ownership. As John was dedicated to his dreams and worked tirelessly to turn them into reality, in 1953 the ever-renowned and celebrated Round Hill was to open its doors to the world of fame, wealth, and creative talent with Noel Coward as its first shareholder.

Round Hill's American and European socialites, literati, and artists built cottages and invested in the hotel


Prominent American and European socialites, literati, and artists were invited to build 'cottages' and to invest in the hotel. Shareholders then included Adele Astaire, Bill and Babe Paley, Lord and Lady Ednam, Mr. and Mrs. Oscar Hammerstein, Clive Brook, Jack and Natasha Wilson, the Marchioness of Dufferin and Ava, Mr. and Mrs. Henry Tiarks, and Viscount and Viscountess Rothermere. The wood-paneled bar is lined today with black and white photographs of the owners and their stylish guests enjoying Round Hill's beach and nightlife.

The original architecture of this notable Montego Bay resort was designed by William Ballard and the signature décor was conceived by Guy Roop. Round Hill was the first resort of its kind in the Caribbean. The hotel operates on the same basis today with 27 villas being owned by individual 'shareholders' chiefly from the U.S. and Europe. One cottage owner, Ralph Lauren, has taken a personal interest in redesigning parts of Round Hill, enhancing its quintessential character. When the owners are not in residence, the cottages are available for rent either as villa suites or as two- to six-bedroom complete villas, most having a uniquely designed private pool set amongst lush tropical landscaping.

The 'cottage colony' model that Pringle had devised at 26 years old has since been widely copied by others all over the world. And, 58 years on in 2011, Round Hill still maintains its special allure due to the inspired capacities of its long-term manager, Josef Forstmayr, who has been able to preserve the past without compromising on the present.

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Historical Highlights

John Pringle, Round Hill Resort
The Honorable John Pringle, -OJ, -CBE
John F. Kennedy at Round Hill
Mike Canfield & JFK
Bing Crosby at Round Hill
Bing Crosby
Adele Astaire at Round Hill
Adele Astaire

Pineapple House

The 36-room hotel was remodeled in 2004 under the guidance of Ralph Lauren, a shareholder at Round Hill.

Villa 3 Details

Sir Noel Coward. Errol Flynn, and Ian Fleming were known to holiday in Jamaica quite often.

Viscount Esmond Rothermere (of the "Daily Mail" newspaper fortune) was the original owner of Cottage 16 at Round Hill. Lady Anne Rothermere was his wife.

In this villa, history tells us that Ian Fleming's 'good friend' Lady Rothermere heated up their relationship until Noel Coward and Ian decided to move down the coast to Orecabessa to start a property similar to Round Hill.

This property was owned by one of their Jamaican friends - Blanche Blackwell. Blanche wanted to develop a similar resort there. Blanche's son, Chris Blackwell, is continuing this dream with the recent opening of Goldeneye in Orecabessa.

Errol Flynn actually bought Navy Island in Port Antonio, another 2 hours drive east of Orecabessa. His widow Patrice Wymore-Flynn still operates her cattle farm there.

Villa 10

John F. Kennedy and Jackie Kennedy preferred to stay in this four bedroom villa with pool because of its privacy, magnificent view, and large lawn which is great for entertaining and children's play. In fact, JFK and Jackie Kennedy honeymooned in this villa.

Villa 11

This spectacular cottage was the setting for the big screen picture by 20th Century Fox, "How Stella Got Her Groove Back", starring Angela Bassett, Taye Diggs and Whoppie Goldberg. Taye Diggs later returned to Round Hill to marry the famous actress Idina Menzel.

Villa 12

Many musicals have been written in this cottage by the original owner Oscar Hammerstein. History tells us that it is at Round Hill where he met Maria von Trapp and "The Sound of Music" was born.

Oscar Hammerstein at Round Hill
Oscar Hammerstein

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