a hand holding a coconut
a woman sitting on a towel
a woman in a bathing suit in water
a woman sitting on a towel on the beach
a group of people serving food
a woman sitting on a floor
a woman in water with mountains in the background
a woman standing on a porch
a group of people sitting on chairs on a beach JFK and Jackie
a group of people posing for a photo Bill Paley, Babe Paley, Truman Capote
a man on a water ski Princess Margaret
a man and woman playing checkers Paul Newman
a man and woman sitting at a table Clark Gable and Liz Pringle
a group of people standing outside a car President Nixon and Governor Conally
a group of people at a table Johnny Cash and Family
a group of women posing for a photo Princess Elizabeth of Yugoslavia & Katrin Casserly
a woman laughing with a man Alfred Hitchcock & Guest
a man in shorts and a shirt with wings Noel Coward
a magazine cover with a woman on the cover Liz Benn
a group of people sitting on chairs on a beach JFK and Jackie
a man and woman playing checkers Paul Newman
a group of women posing for a photo Princess Elizabeth of Yugoslavia & Katrin Casserly
a man and woman sitting at a table Clark Gable and Liz Pringle
a woman laughing with a man Alfred Hitchcock & Guest
a group of people posing for a photo Bill Paley, Babe Paley, Truman Capote
a group of people at a table Johnny Cash and Family
a magazine cover with a woman on the cover Liz Benn
a man in shorts and a shirt with wings Noel Coward
a group of people standing outside a car President Nixon and Governor Conally
a man on a water ski Princess Margaret
a man in a garment on a boat
a man in a suit and hat standing on a stage with a group of kids sitting on grass
a group of kids running through a carnival entrance
a man in a garment with a woman in a room with a table
a man and woman in white dress walking down a walkway
a group of people sitting at tables under a tree
fireworks over a beach
a group of men dancing in front of a house
a group of people in uniform
a chandelier over a table with flowers
Daily Cocktail Journeys

Every festive afternoon at 3pm, the Cocktail Bar turns into a classroom for the well-traveled palate.

Contact us for reservations: restaurantreservations@roundhill.com

Reservations required for all four.
a man wearing a santa garment holding a tennis racket
a man and woman standing next to a large inflatable ball
a massage table with candles and candles on a balcony overlooking the ocean
a bottle of champagne in a bucket and glasses on a tray on a beach
Every Day, A Little Occasion

Between the courts, the spa, and the marquee nights, Round Hill keeps its own rhythm, the kind that turns a stay into a season and strangers into the people you have a drink with every evening.

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Plan Your Stay

Festive Season: December 20, 2026 – January 10, 2027

For Restaurant Reservations: restaurantreservations@roundhill.com

For Hotel Reservations: reservations@roundhill.com

roundhillhotelandvillas festiveseason quad icon

WELCOME HOME

Round Hill has never really been in the business of hotel stays. It has been in the business of returning guests, families who came once in the 1953 and are still coming back with grandchildren who have never known another Christmas. That is what High Society actually means here, not a dress code, a way of belonging. This December, whether you are tracing the same steps Grace Kelly once did, teaching your daughter to waterski in the same bay Princess Margaret loved, or simply finding your spot on the lawn for the tree lighting, you are not a guest passing through. You are part of the story now. Welcome to the family.

One love, The Round Hill family
Round Hill Hotel and Villas is committed to delivering an unforgettable and seamless festive experience. While every detail on this page is accurate at the time of publication, activities, timings, and offerings are subject to change as the season approaches. Please check with the Concierge or Villa Services for the most current schedule during your stay.