Windward Islands Vacation Packages
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Top Windward Islands Vacation Deals
Price found within the past 48 hours. Click for updated prices.
2 bedroom luxury Empire State VIEW
Manhattan
Price was CA $7,236, price is now CA $3,472 per person
CA $3,472
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!
Reviewed on Mar 19, 2026
Windward Islands Hotel Deals
Siesta Hotel
Morne Rouge Street St. George's
The price is CA $137 per night from May 13 to May 14
CA $137
CA $165 total
May 13 - May 14
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
Great valve for money
Reviewed on May 9, 2026
Radisson Grenada Beach Resort
Grand Anse St. George's
Fully refundable
The price is CA $356 per night from May 18 to May 19
CA $356
CA $427 total
May 18 - May 19
includes taxes & fees
8.4/10 Very Good! (1,619 reviews)
💯
Reviewed on May 11, 2026
Coconut Bay Beach Resort & Spa All Inclusive
Eau Piquant Vieux Fort
9.2/10 Wonderful! (1,019 reviews)
This hotel is like a motel. I had bugs in my room and the food was horrible. I wouldn’t recommend this hotel to anyone.
Reviewed on May 11, 2026
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.
Discover the most popular places to visit in Windward Islands
Grand Anse Beach
4.5/5(34 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.
Sandy Beach
4/5(8 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.
Anse Chastanet Beach
4.5/5(33 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
