Windward Islands Holidays

Windward Islands Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was S$679, price is now S$526 per person
S$526
per person
4 May - 5 May
found 1 day ago
Return direct flight included
Seattle (SEA) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (2,008 reviews)
Everything was great and perfectly reasonable in regards to price!

Reviewed on 11 Feb, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was S$718, price is now S$551 per person
S$551
per person
4 May - 5 May
found 1 day ago
Return direct flight included
Seattle (SEA) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,348 reviews)
This hotel was amazing! A great location/beautiful interior/excellent breakfast buffet, but the staff was the best hands down. Every single person who worked there went above and beyond to make our stay fantastic and they were honestly the most friendly people I have ever encountered in my travels. If I could give this review more than 5 stars, I would. Highly recommended!!

Reviewed on 12 Feb, 2026

Roxy Hotel New York

Roxy Hotel New York

4.5 out of 5
Manhattan
Price was S$723, price is now S$586 per person
S$586
per person
4 May - 5 May
found 1 day ago
Return direct flight included
Seattle (SEA) to New York (JFK)
9.4/10 Exceptional! (1,339 reviews)
All of the above11

Reviewed on 25 Jan, 2026

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Top hotels in Windward Islands

Radisson Grenada Beach Resort

Radisson Grenada Beach Resort

4 out of 5
Grand Anse St. George's
Fully refundable
The price is S$344 per night from 14 Mar to 15 Mar
S$344
14 Mar - 15 Mar
includes taxes & fees
8.2/10 Very Good! (1,556 reviews)
We loved every single thing about this resort. There are many reviews about clean room, great breakfast, on the beach, amazing pool. We agree with all of this. What we can add is that you don't need or want to rent a car. The resort is 10 minutes from the airport. Their taxi and local van/bus system ...

Reviewed on 8 Feb, 2026

Radisson Grenada Beach Resort
Siesta Hotel

Siesta Hotel

3 out of 5
Morne Rouge Street St. George's
The price is S$152 per night from 22 Feb to 23 Feb
S$152
22 Feb - 23 Feb
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
Everything was great.

Reviewed on 10 Feb, 2026

Siesta Hotel
Royalton Saint Lucia, An Autograph Collection All-Inclusive Resort

Royalton Saint Lucia, An Autograph Collection All-Inclusive Resort

4.5 out of 5
Gros Islet Gros Islet
Fully refundableReserve now, pay when you stay
The price is S$693 per night from 9 Mar to 10 Mar
S$693
9 Mar - 10 Mar
includes taxes & fees
7.6/10 Good! (1,004 reviews)
We had an amazing time! The staff went above and beyond to make sure all of our needs were met. the staffs that welcome expedia menbers make sure we are very happy with everthing.

Reviewed on 5 Feb, 2026

Royalton Saint Lucia, An Autograph Collection All-Inclusive Resort
See all 6,677 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.

Popular places to visit

Vigie Beach

Vigie Beach

4.5/5(13 reviews)

Join the locals at this city beach where clear waters, white sands and a low-key vibe create a scenic and relaxing experience.

Vigie Beach
Princess Margaret Beach, Bequia Island, St. Vincent and the Grenadines

Port of Port Elizabeth

4.5/5(12 reviews)

Explore the waterfront in Pretoria with a trip to Port of Port Elizabeth. Amble around this relaxing area's beautiful beaches and enjoy its top-notch restaurants.

Port of Port Elizabeth
Pigeon Island National Park

Pigeon Island National Landmark

4.5/5(34 reviews)

Explore the historic British forts for a sense of the fascinating history and climb the two peaks of this headland.

Pigeon Island National Landmark

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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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.