Windward Vacation Packages 2026 from $4,128

Windward flight + hotel vacation packages

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

Le Toiny Hôtel & Beach Club

Toiny

Save 100% on your flight

$4,128

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Gustavia (SBH)

This luxury hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas and airport shuttle. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like full breakfast and valet parking.

Tropical Hotel St Barth

Saint-Jean

$5,496

per person

Nov 20 - Nov 26

found 1 day ago

Roundtrip flight included

Indianapolis (IND) to Gustavia (SBH)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free airport shuttle. Relax with a drink at the poolside bar and enjoy free perks like full breakfast and valet parking.

Hotel Manapany

Anse des Cayes

$9,151

per person

Nov 20 - Nov 26

found 1 day ago

Roundtrip flight included

Indianapolis (IND) to Gustavia (SBH)

A full-service spa, 2 outdoor pools, and a gym are all featured at this luxury hotel. Enjoy a day at the beach snorkeling, or relax with sun loungers. Bring the family and enjoy the children's pool, playground, and arcade/game room.

GYP SEA Saint Barth

Colombier

$8,877

per person

Nov 20 - Nov 26

found 1 day ago

Roundtrip flight included

Indianapolis (IND) to Gustavia (SBH)

A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury hotel. Enjoy the gym and free perks like continental breakfast and valet parking. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.

Le Barthélemy Hotel & Spa

Grand Cul-de-Sac

$4,875

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Gustavia (SBH)

This smoke-free hotel features a private beach, a full-service spa, and 2 restaurants. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Families will appreciate the playground, onsite laundry facilities, and in-room childcare.

Top Windward hotels deals

Christopher Hotel

Pointe Milou, 9 St. Barthelemy

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A full-service spa, 2 restaurants, and an outdoor pool are all featured at this luxury hotel. Families will appreciate the children's pool, onsite laundry facilities, and in-room childcare. Enjoy the gym and free perks like buffet breakfast and valet parking.

Tropical Hotel St Barth

Les Hauts de Saint Jean St. Barthelemy

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This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free airport shuttle. Relax with a drink at the poolside bar and enjoy free perks like full breakfast and valet parking.

Le Barthélemy Hotel & Spa

Baie de Grand Cul de Sac St. Barthelemy

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This smoke-free hotel features a private beach, a full-service spa, and 2 restaurants. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Families will appreciate the playground, onsite laundry facilities, and in-room childcare.

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy

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This luxury hotel features a full-service spa, 2 outdoor pools, and a restaurant. Relax with a drink at the bar/lounge and enjoy free perks like continental breakfast and free self parking. There's a beach bar on site, and a 24-hour front desk and concierge services are also provided.

Le Toiny Hôtel & Beach Club

1 Rue du Toiny St. Barthelemy

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This luxury hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas and airport shuttle. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like full breakfast and valet parking.

Amnios St Barth

Lagon de Grand-Cul-de Sac St. Barthelemy

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This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and airport shuttle. Free self parking, a terrace, and a garden are also offered.

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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.

Photos of local treasures

Browse Windward vacation photos for more inspiration

A red boat on a sandy beach with a rocky hill in the background.

A beach with clear turquoise water, a rocky cliff, and a small island in the distance.

A beach with clear turquoise water, rocky cliffs, and sandy shores.

A coastal landscape with turquoise waters, palm trees, and a hilly background with buildings.

A coastal village with red-roofed buildings, clear turquoise waters, and a stone staircase leading up to the houses.

Frequently asked questions

How much are vacation packages to Windward?

With vacation packages on offer for only $4,128, you won't need to drain your bank balance to travel to Windward. Travelocity is here to help. Bundle up hotels, flights and experiences into a package and land excellent discounts. The more you book, the greater the savings.

Where can I get the best vacation package deals for Windward?

Walking away with an amazing package deal to Windward couldn't be easier with Travelocity. With 400 partner airlines and 1,000,000 properties worldwide, you'll have loads of choice when selecting your flights and hotels.

Why should I book my Windward vacation package with Travelocity?

Because you'll never wander on your own if you lock in your vacation with us, and we offer round-the-clock support and exceptional service to boot. Add to that our Price Match Guarantee and countless experiences and destinations to select from. We're here to help you jet off on the vacation of a lifetime.

Can I save on my Windward car rental if I bundle it with a hotel or flight?

Sure can. And our Windward vacation packages will help you do it. With just a few clicks you can save cash as well as time by booking everything in one place. Pick up the keys to your rental car then set your own course. Looking for things to do? Add some activities or experiences to your package and save on those too.

Which airport is best for Windward?

Princess Juliana Intl. Airport (SXM) is an excellent option for travelers hopping on a plane to Windward. Robert L. Bradshaw Intl. Airport (SKB) and Clayton J. Lloyd Intl. Airport (AXA) also welcome many flights to the region.