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.
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Price was $2,609, price is now $2,166 per person
$2,166
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Saint-Jean
Save 100% on your flight
Price was $28,663, price is now $19,379 per person
$19,379
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
Toiny
Save 100% on your flight
Price was $3,545, price is now $2,604 per person
$2,604
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou
Price was $2,661, price is now $2,198 per person
$2,198
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Gustavia (SBH)
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.
Fouquet's Saint-Barth

Fouquet's Saint-Barth

5 out of 5
Lurin
Save 100% on your flight
Price was $3,903, price is now $3,342 per person
$3,342
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Gustavia (SBH)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free airport shuttle. Relax with a drink at the bar/lounge and enjoy free perks like cooked-to-order breakfast and valet parking.

Top Windward hotels deals

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
$885 nightly
The price is $921 total per night
$921 total
Oct 26 - Oct 27
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
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
$1,004 nightly
The price is $1,054 total per night
$1,054 total
Nov 11 - Nov 12
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 Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Baie de Grand Cul de Sac St. Barthelemy
$2,349 nightly
The price is $2,459 total per night
$2,459 total
Nov 1 - Nov 2
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
Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
1 Rue du Toiny St. Barthelemy
$1,275 nightly
The price is $1,338 total per night
$1,338 total
Oct 29 - Oct 30
Total with taxes and fees
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.
Pool
Breakfast included
Amnios St Barth

Amnios St Barth

Lagon de Grand-Cul-de Sac St. Barthelemy
Get rates
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.
Pool
Pet friendly
Le Sereno

Le Sereno

5 out of 5
Grand Cul de Sac BP 19 St. Barthelemy
Get rates
This smoke-free hotel features a private beach, a full-service spa, and a restaurant. Dine at the beachfront restaurant and relax with beach umbrellas. Enjoy the outdoor pool and free perks like full breakfast and free self parking.
On private beach
Pool
Don't see what you're looking for?
See all available properties in Windward
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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 $2,166, 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.