Windward Islands Holidays from NZ$2,902

Book a Hotel + Flight or Car together to unlock savings

The Latest Windward Islands Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

Manhattan
NZ$2,902
per person
23 Nov - 27 Nov
found 18 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
8.8/10 Excellent! (7,930 reviews)
OYO Times Square

OYO Times Square

Manhattan
NZ$3,218
per person
30 Oct - 5 Nov
found 2 hours ago
Return flight included
Wellington (WLG) to New York (JFK)
6.8/10 (2,082 reviews)
Lovely experience for my first time in NYC

Reviewed on 26 Sept 2026

Hotel 32 32

Hotel 32 32

Manhattan
NZ$3,669
per person
30 Oct - 5 Nov
found 2 hours ago
Return flight included
Wellington (WLG) to New York (JFK)
8/10 Very good! (2,547 reviews)
Empire Hotel

Empire Hotel

Manhattan
NZ$4,143
per person
30 Oct - 5 Nov
found 1 day ago
Return flight included
Wellington (WLG) to New York (JFK)
7.6/10 Good! (7,152 reviews)
The Evelyn Hotel

The Evelyn Hotel

Manhattan
NZ$2,960
per person
23 Nov - 27 Nov
found 18 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
9.4/10 Exceptional! (1,368 reviews)

Windward Islands Holiday

Our pick of the best Windward Islands Hotel Deals

Siesta Hotel

Siesta Hotel

Morne Rouge Street St. George's
NZ$172
30 Sept - 1 Oct
includes taxes & fees
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
NZ$1,058
28 Sept - 29 Sept
includes taxes & fees
Secrets St. Lucia Resort & Spa All Inclusive Adults Only
Coconut Bay Beach Resort & Spa All Inclusive

Coconut Bay Beach Resort & Spa All Inclusive

Eau Piquant Vieux Fort
Get rates
Coconut Bay Beach Resort & Spa All Inclusive
See all 6,887 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 beach with two surfboards leaning against a post, a clear blue sky, and calm sea with boats in the distance.
Photo by Catherine Carroll

Grand Anse Beach

9.6/10 (1,447 reviews)
If a restful holiday is part of your travel plans, Grand Anse Beach might be the perfect place to visit 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 beach with a sandy shore, calm water, and sailboats.

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 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 terrace with wicker furniture overlooking a coastal landscape with mountains and the ocean.

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 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 holiday is part of your travel plans, Sandy Beach might be the perfect place to visit during your trip to Vieux Fort. While in this romantic area, you can savour the top-notch restaurants.
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A coastal marina with sailboats, surrounded by lush greenery and a hillside with buildings.

Marigot Bay

8.8/10 (598 reviews)
Commune with nature and explore the great outdoors at Marigot Bay during your travels in Marigot Bay. While in this relaxing area, you can savour the top-notch restaurants.
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A marina at sunset with boats docked and palm trees in the foreground.
Photo by Nerdin St Rose

Rodney Bay Marina

8.8/10 (1,500 reviews)
Explore the waterfront in Gros Islet with a trip to Rodney Bay Marina. Stroll along the beautiful beaches or visit the shops in this relaxing area.
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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.