Just over fifty years ago when Round Hill was an undeveloped, lush jungle rising over the sea, one man had the good fortune and discernment to select the most treasured lot of all. This priceless piece of land, which was favored by the sun and prevailing trade winds, also featured one of the most spectacular views in all of the Caribbean. The home was built with a vision of joyful family gatherings, romantic getaways and friends celebrating the complete vacation experience. Thus, Hillside was born. The result is a home privately tucked into the east side of Round Hill yet minutes from the amenities of the famous resort.

The large living room opens to a spacious veranda overlooking the pool and ten-mile stretch of sea that separates Round Hill from the town of Montego Bay. Each night the lights of Montego Bay dance across the water, forming part of the magic of Hillside. 

Candlelight dinners are served in the outdoor dining arbor adjacent to the lighted garden. Later, Stanley, the butler, serves coffee and after-dinner drinks on the veranda, giving guests another experience of the mesmerizing view and ocean breezes before retiring.

Hillside Cottage boasts one of the finest staffs on the North Coast of Jamaica. Fay, the cook, has been here for 13 years and is gifted with talents that rival the island's finest chefs.  Hillside's Butler, Stanley, has been with the house for over 25 years, serves meals and drives guests on desired excursions. The Housekeeper, Sheila, performs daily maid service and decorates with fresh tropical flowers. The laundress, Ruth, washes clothes and towels daily, and the gardener, Melton maintains the pool and grounds in immaculate condition.

The Round Hill beach and hotel are a short walk down the tree-lined lane,  just outside Hillside's door. The hotel offers free tram service for the one-minute ride to the beach.  Hillside renters enjoy the security and full amenities offered by Round Hill Resort as well as the complete privacy of their own fully staffed villa.