Windward Islands Trips (flight + hotel)

Top Flight + Hotel Deals in Windward Islands

Price found within the past 48 hours. Click for updated prices.
Sela V Hotel

Sela V Hotel

P168,243
per person
Sep 21 - Sep 26
found 18 hours ago
Roundtrip flight included
Manila (MNL) to New York (JFK)
9.8/10 Exceptional! (92 reviews)
Everything about this hotel was beautiful! The interior design, amenities, and sweet staff made this into the best last minute staycation ever.

Reviewed on Aug 12, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

Manhattan
P197,035
per person
Sep 21 - Sep 26
found 18 hours ago
Roundtrip flight included
Manila (MNL) to New York (JFK)
9.2/10 Wonderful! (3,841 reviews)
Our plane was delayed by about 5 hours and the staff was understanding and helpful with checking in and getting us to our room.

Reviewed on Aug 12, 2026

LGA AIRPORT

LGA AIRPORT

Queens
Save 100% on your flight
P474,715
per person
Sep 21 - Sep 26
found 18 hours ago
Roundtrip flight included
Manila (MNL) to New York (JFK)
10/10 Exceptional! (2 reviews)
The best airbnb Ive stayed at in New York with the best price for our family of 6. The place was so clean, amenities looked brand new. It had a homey feel to it, my kids didnt want to leave. We will definently be booking again in the future.

Reviewed on Dec 24, 2025

Westgate New York Grand Central

Westgate New York Grand Central

Manhattan
P232,775
per person
Sep 21 - Sep 26
found 18 hours ago
Roundtrip flight included
Manila (MNL) to New York (JFK)
9/10 Wonderful! (3,225 reviews)
no complaints

Reviewed on Aug 12, 2026

Duane Street Hotel Tribeca, Belvilla District 6 Formerly Sonder

Duane Street Hotel Tribeca, Belvilla District 6 Formerly Sonder

Manhattan
P194,279
per person
Sep 21 - Sep 26
found 18 hours ago
Roundtrip flight included
Manila (MNL) to New York (JFK)
8.2/10 Very Good! (912 reviews)
Ravi was phenomenal and so helpful during the process and welcoming after I checked out! Appreciate the stay!

Reviewed on Aug 12, 2026

Top hotels in Windward Islands

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
P6,103
P7,323 total
Sep 7 - Sep 8
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
P36,694
P36,694 total
Sep 8 - Sep 9
includes taxes & fees
Secrets St. Lucia Resort & Spa All Inclusive Adults Only
See all 6,826 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.