Round Hill Hotel & Villas

• Price Guidance:
• $$$$$

The Round Hill Hotel & Villas in has hosted John F. Kennedy, Paul Newman, Grace Kelly, and Ralph Lauren. Ralph loved it so much he bought into, and helped expand, this resort, adding his signature touch to the decor of one of my favorite Jamaica resorts.

The Round Hill is just 25 minutes away from Montego Bay Airport, with different accommodation options from hotel rooms, to very stylish individual bungalows.

Round Hill Hotel & Villas

Go for the Lauren-designed oceanfront rooms (akin to more traditional hotel rooms), or opt for the privacy of a complete villa with your own dedicated staff.

There’s old-school beachside dining at the Seaside Terrace, with excellent food and local bands many nights. Whether you’re sipping on a handcrafted cocktail or relishing a fresh-off-the-boat seafood catch, each bite lives up to the hotel’s reputation.

The beach sets the standard for laid back luxury chill, with a beach-side bar that looks like it’s right out of a postcard. I loved almost everything about this place!

Highs:

• The great design and luxury of the villas
• The beach + beach bar
• Laid back vibe

Lows:

• Not the most expensive place, but still pricey
• There’s not much close by, so expect to eat most, if not all, your meals at the resort

Good Hope Villas

• Price Guidance:
• $$$$$

Is it a hotel, Airbnb, or something else? I’m not sure. You can book a single room, or book the whole place. But please be aware that it is often booked out for retreats, so you’ll find good chunks of the year when there is no availability.

Good Hope is in the hills of Trelawny, 45 minutes from Montego Bay airport, at the entry of Jamaica’s famous Cockpit country.

This beautiful 300 year old sugar plantation sits on hundreds of acres with hiking and horseback riding close by. There’s also local pottery on site.

Good Hope Villas

You can stay in the Great House or the Carriage House which is steps below the Great House. There is also an individual building/room behind the Great House which I thought was the nicest room in the place.

Horseback ride, hike, explore the Cockpit country, learn pottery, or chill at one of the hotel’s two pools. They also have their own private beach 20-30 min away with changing rooms, chairs, picnic tables and someone on hand to serve cold drinks.

This is the opposite of Jamaica’s mega-resorts, a true gem that I loved.

Highs:

• The historic architecture and tasteful restoration
• The setting in the tropical mountains
• The staff

Lows:

• It’s not a typical hotel experience, so won’t work for everyone