Windward Islands Vacations from ₩2,559,756

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The Latest Windward Islands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

Downtown Jersey City
₩2,559,756
per person
Oct 3 - Oct 9
found 5 hours ago
Roundtrip flight included
Seoul (ICN) to New York (JFK)
8.6/10 Excellent! (1,690 reviews)
Freehand New York

Freehand New York

Manhattan
₩3,186,654
per person
Oct 3 - Oct 9
found 5 hours ago
Roundtrip flight included
Seoul (ICN) to New York (JFK)
8.6/10 Excellent! (2,091 reviews)
Canopy by Hilton Jersey City Arts District

Canopy by Hilton Jersey City Arts District

Downtown Jersey City
₩2,619,298
per person
Oct 3 - Oct 9
found 5 hours ago
Roundtrip flight included
Seoul (ICN) to New York (JFK)
9.2/10 Wonderful! (1,008 reviews)
OYO Times Square

OYO Times Square

Manhattan
₩2,757,076
per person
Oct 3 - Oct 9
found 5 hours ago
Roundtrip flight included
Seoul (ICN) to New York (JFK)
6.8/10 (2,053 reviews)
Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

Manhattan
₩3,024,545
per person
Oct 3 - Oct 9
found 5 hours ago
Roundtrip flight included
Seoul (ICN) to New York (JFK)
8.6/10 Excellent! (2,145 reviews)
Staff amazing and room clean

Reviewed on Aug 12, 2026

Find the Best Windward Islands Vacation Packages

Windward Islands Hotel Deals

Coconut Bay Beach Resort & Spa All Inclusive

Coconut Bay Beach Resort & Spa All Inclusive

Eau Piquant Vieux Fort
9.2/10 Wonderful! (1,110 reviews)
"Great"

Reviewed on Aug 12, 2026

Get rates
Coconut Bay Beach Resort & Spa All Inclusive
Siesta Hotel

Siesta Hotel

Morne Rouge Street St. George's
₩141,903
₩170,283 total
Sep 2 - Sep 3
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"w"

Reviewed on Aug 11, 2026

Siesta Hotel
Secrets St. Lucia Resort & Spa All Inclusive Adults Only

Secrets St. Lucia Resort & Spa All Inclusive Adults Only

1 Choc Bay Gros Islet
Fully refundableReserve now, pay when you stay
₩846,073
₩846,073 total
Sep 8 - Sep 9
includes taxes & fees
Secrets St. Lucia Resort & Spa All Inclusive Adults Only
See all 6,880 properties in Windward Islands
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Windward Islands attractions

A lifeguard tower on a beach with turquoise water and a white picket fence.

Grand Anse Beach

9.6/10 (1,447 reviews)
If a restful vacation is part of your travel plans, Grand Anse Beach might be the perfect place to seek out during your trip to Grand Anse. Make time to visit the area's shops, or simply enjoy its top-notch restaurants.
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A coastal town with colorful houses, a mountain, and a rainbow over the sea.

Gros Piton

9.6/10 (803 reviews)
Explore one of the most famous sites in Soufrière, a gigantic volcanic peak rising from the sea that attracts visitors from all over the world.
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A beach at sunset with waves, palm trees, and a silhouette of a person walking.
Photo by Davz

Sandy Beach

7.8/10 (211 reviews)
If a restful vacation is part of your travel plans, Sandy Beach might be the perfect place to seek out during your trip to Vieux Fort. While in this romantic area, you can savor the top-notch restaurants.
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A beach with clear turquoise water, boats, and a distant mountain.

Reduit Beach

9.0/10 (1,288 reviews)
Ride a Jet Ski, laze on the sand and enjoy a cool drink at the bar on this scenic beach set against a backdrop of verdant hills.
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A coastal landscape with a prominent mountain peak, lush green hills, and calm blue waters.

Anse Chastanet Beach

9.2/10 (538 reviews)
Enjoy a pleasant Caribbean beach day surrounded by abundant natural beauty. Relax sunbathing on dark sand and snorkeling in crystal-clear waters.
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A beach with clear turquoise water, sandy shore, and a hill with buildings in the background.
Photo by Amir

Morne Rouge Beach

9.0/10 (550 reviews)
Why not spend a carefree afternoon at Morne Rouge Beach during your travels in Grand Anse? Make time to visit the area's shops, or simply enjoy its top-notch restaurants.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.