Exclusive Offer

Hillside House on Round Hill | May Getaways

Hillside House on Round Hill | May Getaways

Save up to 20% on your May 2026 getaway — the perfect time to travel and save.

Valid for new bookings made from now to April 30, 2026, for travel from May 01, 2026, to May 30, 2026. Blackout dates may apply. Five-night minimum booking required. Subject to availability and may not be combinable with other offers. Additional restrictions may apply; please call for complete details.
10 Guests 5 Bedrooms 5 Bathrooms

Hillside House on Round Hill

Jamaica / Montego Bay

Perched atop the legendary Round Hill Estate, Hillside House embodies the timeless charm of Old Jamaica paired seamlessly with modern luxury. This crowning jewel has long been a show-stopper, celebrated for its breathtaking panoramic views and cooling trade winds that sweep effortlessly through the property. Thoughtfully designed with families in mind, Hillside House offers inviting, unpretentious elegance — a relaxed yet refined retreat created for savoring the very best of island living.

Our Exclusive Offers:
  • Hillside House on Round Hill | May Getaways
View Villa

Specials by Destination

Antigua (1)
Barbados (8)
Belize (1)
British Virgin Islands (2)
Dominican Republic (1)
Florida (1)
Grand Cayman (2)
Italy (1)
Jamaica (7)
Los Cabos (2)
Riviera Maya (1)
South Carolina (1)
St. Lucia (1)
St. Martin (6)
Tanzania (1)
Turks & Caicos (17)