Montpelier Plantation & Beach

Late September to mid-December is prime time to score some of the best deals at great hotels in the Caribbean—for as little as $95 per night in Jamaica to $150 for an all-inclusive getaway in the Dominican Republic. And while it's true that the Atlantic hurricane season adds a small element of risk, November and December are usually lovely, and this is the time to score the best prices if you're willing to book.

Here are 10 cheap hotel rates in the Caribbean to consider. Just play with your dates to find the best deal.

Jakes Hotel, Treasure Beach, Jamaica — from $95

For bohemian camaraderie with good food and fun music (plus the beauty of this non-touristy stretch of Jamaica’s south coast), check into one of the 40 cheerful and quirky garden-view rooms at Jakes Hotel. There’s something authentic, organic, and personal about a place that appeals equally to the everyman and the A-lister. The largest villas are priced at about $700/night in the fall—but nobody cares who’s paying what.

Grand Bahia Principe Punta Cana, Dominican Republic — from $150

That $150 price tag is all-inclusive—for two people. The 756-room Grand Bahia Principe Punta Cana on palm-tree-lined Bavaro Beach is a great solution if you have a fixed budget and don’t want to be tempted to spend more. The rates include all food (there are six restaurants) and drinks (at four bars), two pools, a children’s water park, one hour of free non-motorized watersports rentals daily, nightly entertainment, and access to the amenities at Grand Bahia Principe Bavaro and Grand Bahia Principe Turquesa.

Sugar Ridge, Antigua — from $150

The 550-square-foot Deluxe King with Plunge Pool—which features a veranda with a daybed and private pool (as noted) with panoramic views—can be yours for 45 percent off if you book and travel by Oct. 18. Sugar Ridge, a 60-room luxury resort located on a hillside on Antigua’s west coast, offers two restaurants, three pools, a 2,500-square-foot Aveda spa, and a shuttle to Turner’s Beach or Valley Church Beach, with service staff on hand for drinks and snacks.

Santa Barbara Beach & Golf Resort, Curacao — from $159

If you’re a beach lover and he’s a golfer (or vice versa), take a week-long getaway at the 350-room Santa Barbara Beach & Golf Resort. Located on the sunny and colorful Dutch island of Curacao, the resort is offering this low rate for a spacious Resort View Room for those who book between now and December 20th. Also on the 2,000-acre property: four restaurants, tennis courts, a spa, a white-sand beach, three pools, and miles of hiking trails.

Sheraton Old San Juan Hotel, Puerto Rico — from $142

Sometimes it’s not about the beach. If access to the dining, shopping, culture, and the historic ambience of Old San Juan are what you’re after, the affordable rates at the 240-room Sheraton Old San Juan will leave you with money to spend on all that the city’s colonial heart has to offer—and boost the local economy as it continues its recovery from 2017’s Hurricane Maria. When it’s time to relax, you can order cocktails and snag a chaise at the rooftop pool.

Ti Kaye Resort & Spa, St. Lucia — from $168

Romance and seclusion usually don’t come cheap, but if you’re looking for both, book an Ocean View Room at the adults-only Ti Kaye Resort & Spa for a stay from now until Nov. 30.  Located in traditional Caribbean-style wooden cottages (just 33 in all) with a four-poster bed, private outdoor shower, and a deck with two rocking chairs and a double hammock—all with views of the sea—these accommodations on St. Lucia are designed to seduce. There’s free wifi, too (not that you’ll need it).

Hilton Barbados Resort, Barbados — from $147

Barbados isn’t known for its bargains, but the 355-room Hilton Barbados Resort has always been a reliable go-to for an affordable room overlooking one of the island’s prettiest beaches. The deal: Stay four nights and get the fifth free, which brings the rate for a Bay View Room to less than $150/night. While here, you can enjoy four restaurants, a spa, and an infinity-edge pool with waterfalls and whirlpools.

Montpelier Plantation & Beach, Nevis — from $150

Now though Oct. 31, book the "Live Like a Local" rate on a spacious 535-square-foot Premier Room at this historic inn on the tranquil island of Nevis, and you’ll enjoy a king-size bed and terrace with a garden view. Offering just 19 rooms, Montpelier Plantation & Beach is located on 60 acres of lush tropical hillside and has two great restaurants (you can also dine privately inside a 300-year-old sugar mill) and a serene pool. The property will also transport you to its nearby private beach.

Hotel Bakoua, Martinique — from $162

Perhaps you’re looking for a new island to experience—one with a decidedly French vibe, colorful cultural traditions, and delicious Creole cuisine. If so, say “oui” to a Garden View Room at the 139-room Hotel Bakoua, which is set on scenic peninsula overlooking Martinique’s Fort de France Bay. It offers splendid views, contemporary design, an infinity-edge pool, and easy beach access, as well as two casual restaurants that specialize in seafood.

Holiday Inn Resort: Aruba Beach Resort & Casino — from $133

Sun-seekers love Aruba for so many reasons, and this property covers them all. Located on popular Palm Beach, those who enjoy flavorful cuisine and rolling the dice after dark will have a blast at the Holiday Inn Resort: Aruba Beach Resort & Casino, which boasts 590 rooms, five restaurants, multiple pools and whirlpools, a spa, a kids’ program, and a casino.

Find The Best Cruises
Find a cruise

Find the best deals!

Click on multiple sites to get the lowest prices

Click on multiple sites to get the lowest prices

Take Our Survey!

We want to deliver more of what you want, the deals you love, and stories that inspire you. It will only take a few minutes.