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Caribbean Island of the Month
February
Perched on a lush hillside overlooking the turquoise waters of Montego Bay, Round Hill Hotel and Villas blends timeless elegance with authentic Jamaican charm. This iconic resort, once a private haven for Hollywood legends, features beautifully restored Ralph Lauren-designed oceanfront rooms and luxurious private villas with pools and dedicated staff. Surrounded by 110 acres of tropical gardens and pristine coastline, guests enjoy gourmet dining with farm-to-table ingredients, a world-class spa nestled in a historic 18th-century plantation house, and warm, attentive service. Whether lounging by the infinity pool, exploring the reef, or savoring sunsets on the beach, Round Hill offers a truly unforgettable Caribbean escape.
Things to Do
Round Hill Hotel and Villas offers a diverse array of activities for every interest. Guests can enjoy adventures like ziplining and bamboo rafting or unwind with sunset cruises and beach lounging. On property, the resort features pickleball, tennis, and a variety of watersports. Guests can also elevate their game during Fantasy Week clinics led by former ATP stars Guillermo Cañas, Tommy Robredo, and Dominik Hrbaty, all just minutes from Montego Bay’s attractions.
Dining
Dining at Round Hill is a culinary delight, featuring 11 distinctive food and beverage outlets led by Executive Chef Martin Maginley, with a focus on fresh, locally sourced ingredients. Guests can enjoy gourmet dining, casual beachside fare, and daily Food & Beverage Activations, including tastings and mixology sessions. The A Culinary Constellation series further elevates the experience with guest chefs, including a Spring Break 2026 residency by James Beard Award–winning chef Rocco DiSpirito.
Wellness
The Spa at Round Hill is a sanctuary of relaxation, set in a restored 18th-century home. Offering Elemis aromatherapy treatments, an open-air yoga pavilion, and a state-of-the-art fitness center, guests can indulge in personalized wellness experiences amidst lush tropical surroundings. In addition to these signature services, the resort partners with expert practitioners to provide curated wellness sessions — including Pilates, one-on-one healing work, and mindfulness practices that leave guests feeling truly rejuvenated.
Book now through 3/15/26
for travel now through 10/31/26 (Blackout Dates Apply)
Classic Vacations offers customers access to vacation packages, which are provided by separate and independent vendors of travel services. Classic Vacations does not operate, control, or otherwise provide the services of the independent travel vendors. Offers are valid on new bookings only and cannot be applied to existing reservations. Prices shown are per person, land-only, based on double occupancy, and do not include optional excursions or other optional items unless expressly stated otherwise. Obvious errors and misprints are not binding. Offers are subject to availability at the time of booking and may be modified, replaced, or discontinued without prior notice. Prices are subject to change until full payment is received. Blackout dates, minimum night stays, air booking requirements, seasonal surcharges, resort fees (if applicable), and other restrictions may apply. Customers are responsible for purchasing travel insurance. Some offers may require the purchase of Classic Vacations’ Travel Smart Plan or a travel waiver for eligibility. Customers are responsible for paying any cancellation fees. Offers are not valid for Group Travel unless explicitly stated. Booking and travel dates may vary by offer. Additional promotions and alternative departure dates may be available, potentially resulting in different pricing or hotel inclusions. Customers are responsible for all applicable taxes and fees associated with a booking, including those associated with complimentary nights at hotels, where applicable. For properties where Classic Vacations offers dynamic pricing rates, prices are subject to change based on market conditions and external factors beyond Classic Vacations’ control. Additional terms and conditions may apply to specific offers. Please refer to the individual offer details for full terms. California Seller of Travel # 2079429. Registration as a seller of travel does not constitute approval by the State of California.