While trends in travel come and go, Round Hill Hotel and Villas has been a much-needed respite for luxury travelers since 1953.  Jamaica-born entrepreneur, John Pringle, had a vision to take the ’boutique’ concept both onto another level and into a new domain which quickly became a jet-set favorite that has attracted guests including Adele Astaire, the Kennedys, Oscar Hammerstein, Johnny Cash, Paul McCartney, and members of the British royal family for its tranquility and privacy.

In a quick 30-minute coastal drive from the airport in Montego Bay, guests enter the lush 110-acre peninsula, a former sugarcane plantation and home to pineapple groves (which inspired the Round Hill logo), maintaining its secluded ambiance and classic charm that is appealing to travels now more than ever.

It is refreshing to have a property with such an engaged Managing Director, Josef Forstmayr, and team of highly skilled and dedicated staff that work tirelessly to preserve the history and legacy of this

iconic resort, while staying at the forefront of travel trends.  Round Hill retains a classic, plantation-style design, colonial-inspired furnishings, and the original checkered floors and an 18th-century chandelier with candles that are lit nightly in the lobby.  Classic meets current needs with having superb Wi-Fi strength, and up-to-date COVID safety protocols to ensure the guests comfort and safety.

Accommodations

The resort consists of 36 deluxe guestrooms that were redesigned by Ralph Lauren and 27 hillside villas that can be divided into 96 suites.

The Pineapple House

These hotel-style units are split across two sea-facing floors and are perfect for those wanting to be steps from the beach and/or those looking for the most cost-effective room option.

The upper level (ocean view) rooms have towering cathedral ceilings and large and louvered windows that fold back to expose the turquoise sea 

  • The lower level (ocean front) rooms have traditional ceilings and patios featuring quaint, secluded balconies.
  • All rooms are outfitted with a king or two double beds, and many of the rooms feature connecting doors (that can be confirmed at time of booking) making them perfect for families with children. 
  • Keep in mind, ages 13 and older is considered an adult when booking. 
  • There are two walkout rooms that are saved for guests with mobility issues.
Villas (Cottages)

The villas were originally called cottages, so the name may be used interchangeably and is not to be confused with different room types. While no villas are on the beach, the design has them dotting the hillside, offering privacy, gorgeous ocean views and are often a short stroll (or golf cart ride, if requested) down to the main amenities. 

All villas are individually owned. Each are decorated differently, though expect a similar plantation-style design throughout. 

  • Many of the cottages have been fully upgraded and expanded, including modern fixtures and amenities, while still maintaining the authenticity that they were built upon. 
  • The villas come with spacious living areas, furnished outdoor spaces, kitchens, and many have private pools, providing perfect seclusion. 
  • Options range from 1 to 6 bedrooms. 
  • Each complete villa has its own dedicated cook, housekeeper and gardener, with the larger villas having additional staff.

Dining

Since travelers often have different views about meal plans, Round Hill guests have the ability choose from European plan to a range of meal/drink packages. It is best to discuss the options with your travel advisor in advance, as one of the possibilities must be booked prior to arrival. Children age 4-12 receive a 50% discount on meal plans.

Guests will enjoy signature dining by James Beard award-winning Executive Chef Martin Maginley.

Breakfast

Cottage Suites & Villas will have housekeepers prepare a homemade breakfast served in the privacy of your accommodation. Lodging guests in in the Pineapple House may order breakfast through room service.  The Grill is also open for those wanting to enjoy their meal from the rooftop restaurant.

Suggestions: Banana, pineapple or coconut pancakes

Lunch

Choose from the Seaside Terrace, pool or beach bars or Beach Grill (seasonal).

Suggestions: Round Hill nachos and jerk chicken summer rolls

Afternoon Tea

A traditional and formal Afternoon Tea, featuring home-made sandwiches, cakes, scones, tea and coffee, is served daily from 4:00 – 5:00pm at the Cocktail Bar.  (no charge for this daily service)

Dinner

With two main dining areas, The Restaurant at Round Hill and Seaside Terrace, guests can also attend special events throughout the week.

MONDAY – Beach Barbecue Buffet

WEDNESDAY – Manager’s Cocktail Reception

THURSDAY & SUNDAY – Farm-to-Table Dinner at the Grill

FRIDAY – Jamaica Night

Dress Code: Long trousers for gentlemen at dinner (except Mondays)

Early dining from a children’s menu is available.  A reduced meal plan can be arranged on request.

Currently operating at a reduced capacity, reservations for dinner are required to facilitate the appropriate physical distance between guests, with temperatures taken before the start of each reservation.

Specialty Dining

Additional dining services include private chef in-villa meals with limited face-to-face interactions and specially curated private experiences on-property such as a beach barbecue or romantic dinner in the gazebo, among other offerings.

Suggestion: In-villa private chef preparing a Jamaican feast.

Round Hill’s on-site organic garden provides many of the fresh vegetables and herbs used to prepare dishes. The garden is located at the top of the bluff and guests are able to visit the garden and experience the sweeping views of both Round Hill Bay and Montego Bay. A private chef’s tour and lunch in the garden can also be arranged.

Activities

Round Hill offers the best of both worlds, allowing guests to have seclusion and privacy, with all the amenities and services of a 5-star resort.

A schedule of the rotating daily activities and dining options is posted in the lobby and will soon be available on the new resort app.

Water
  • Coved beach with calm water, loungers, umbrellas and a trampoline
  • Infinity pool with a shallow section for kids overlooking the ocean
  • Non-motorized water sports (snorkeling, kayaking, paddle boats)
  • Motorized water sports for an additional fee (water skiing and tubing, hobie cat sailing, speedboat trips, sport fishing, scuba diving)
  • Guided glass bottom boat ride available daily (weather permitting)
Land
  • Five tennis courts, including three new Har-Tru courts
  • Shuttle to Tryall Golf Club, one of the Caribbean’s finest golf courses
  • Jogging path with Fit-Trail® offering workout stations along the jogging trail
  • Shuttle to Montego Bay for shopping
  • Heritage hike (offered on Sundays)
  • Area where local artisans sell goods such as handbags and wood carvings (bring cash and support local artists)
  • Pineapple Room has a large TV and comfy couches
  • Library offers a collection of books and additional seating
Kids
  • Pineapple Kids Club is available with supervision for children ages 3 through 6
  • Children who are not potty trained must be accompanied by a parent or a babysitter
  • 7-Up Club satisfies the desires of children 7 years and older, including teens
  • Both programs are open daily from 9 a.m. to 5 p.m.
  • After-hours nanny services are available at an additional charge
Spa & Fitness
  • Adult-only escape on 10 beachfront acres
  • Unique setting in a beautifully restored 18th century plantation house
  • Seven spacious treatment rooms including one couple’s suite
  • Luxurious, secluded outdoor treatment area set amidst abundant tropical gardens
  • Spa therapists will also provide in-villa spa services upon request
  • Spa utilizes the renowned Elemis product line
  • Spacious lounge areas on the oceanfront lawn
  • Pool terrace complete with incredible views, lunch and beverage service
  • An ocean view Fitness Centre and open-air Yoga Pavilion
  • Fitness center boasts an array of top of the line Cybex Fitness equipment
  • Reserve a session with one of the professional personal trainers or work out solo
  • Fitness classes led by seasoned instructors, including yoga and body sculpting

🌴 🌴 🌴 🌴

Round Hill Hotel and Villas is an exclusive and beloved resort that exudes old-world Caribbean charm. It is ideal for those looking for privacy and understated luxury.  Steeped in rich history, Round Hill has hosted many historical moments including Cottage 25 John F. Kennedy edited and rehearsed his now famous inauguration speech by the pool; in Cottage 12 Oscar Hammerstein wrote the lyrics for “The Sound of Music”; and Cottage 11 was the setting for the movie “How Stella Got Her Groove Back”.  Make sure to take a look at the black and white photos of famous guests of years past dotting the walls of the Cocktail Bar.

Let’s plan your getaway to this exclusive address that is nestled in a lush tropical hillside along a private bay of turquoise waters where paradise is found, and experiences become lasting memories.

Be sure to check out my last blog covering the pre-travel process going to Jamaica – Click Here

Contact Us:

Jamie Jackson: (336) 263-1977 or [email protected]

Luxury Travel Advisor and Virtuoso Wellness Travel community member at Wanderlust Travel Boutique

At Wanderlust Travel Boutique, we will create a truly personalized, hassle-free vacation with a comprehensive itinerary, so you can enjoy an unforgettable experience.

If not now, when?

https://www.virtuoso.com/advisor/jamiejackson

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