Deals on vacations and trips to Windward

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Windward flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
Toiny
Price was $2,951, price is now $2,623 per person
$2,623
per person
Oct 16 - Oct 19
found 9 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Gustavia (SBH)
This smoke-free hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. Enjoy a day at the beach surfing, or relax with sun loungers. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like full breakfast and valet parking.
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Grand Cul-de-Sac
Price was $3,606, price is now $3,295 per person
$3,295
per person
Oct 22 - Oct 25
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) 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

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
$844 nightly
The price is $879 total per night
$879 total
Aug 4 - Aug 5
Total with taxes and fees
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.
Pool
Breakfast included
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy
$2,301 nightly
The price is $2,416 total per night
$2,416 total
Aug 1 - Aug 2
Total with taxes and fees
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.
Pool
Breakfast included
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Baie de Grand Cul de Sac St. Barthelemy
$1,880 nightly
The price is $1,961 total per night
$1,961 total
Aug 15 - Aug 16
Total with taxes and fees
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.
On private beach
Pool
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
$771 nightly
The price is $809 total per night
$809 total
Jul 30 - Jul 31
Total with taxes and fees
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.
Pool
Breakfast included
Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
1 Rue du Toiny St. Barthelemy
$957 nightly
The price is $1,004 total per night
$1,004 total
Aug 17 - Aug 18
Total with taxes and fees
This smoke-free hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. Enjoy a day at the beach surfing, or relax with sun loungers. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like full breakfast and valet parking.
Pool
Breakfast included
Lil' Home

Lil' Home

548 Route de Dévêt, Devet St. Barthelemy
Get rates
An outdoor pool is featured at this cottage, along with concierge services. Take advantage of the free self parking.
Pool
Kitchen
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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 $2,623, 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.