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.
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Saint-Jean
Save 100% on your flight
Price was $3,609, price is now $2,648 per person
$2,648
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip non-stop 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 $4,047, price is now $3,070 per person
$3,070
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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.
GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Colombier
Price was $3,392, price is now $2,897 per person
$2,897
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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.
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Price was $3,422, price is now $2,934 per person
$2,934
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Grand Cul-de-Sac
Price was $5,468, price is now $4,887 per person
$4,887
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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
$886 nightly
The price is $923 total per night
$923 total
Jun 28 - Jun 29
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
$2,208 nightly
The price is $2,318 total per night
$2,318 total
Jun 9 - Jun 10
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
$1,866 nightly
The price is $1,953 total per night
$1,953 total
Jun 20 - Jun 21
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.
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
$710 nightly
The price is $745 total per night
$745 total
Jul 3 - Jul 4
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.
Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
1 Rue du Toiny St. Barthelemy
$1,162 nightly
The price is $1,221 total per night
$1,221 total
Jun 16 - Jun 17
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.
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
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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.

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Frequently asked questions

How much are vacation packages to Windward?
With vacation packages on offer for only $2,648, 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.