Deals on vacations and trips to Windward

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Windward flight + hotel vacation packages

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Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Save 100% on your flight
Price was $4,806, price is now $3,224 per person
$3,224
per person
May 18 - May 24
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
Save 100% on your flight
Price was $5,095, price is now $3,482 per person
$3,482
per person
Apr 28 - May 4
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) 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
Save 100% on your flight
Price was $6,641, price is now $4,885 per person
$4,885
per person
May 18 - May 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Gustavia (SBH)
A full-service spa, 2 restaurants, and 2 outdoor pools are all featured at this luxury hotel. 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
Save 100% on your flight
Price was $4,495, price is now $3,521 per person
$3,521
per person
May 18 - May 24
found 1 day ago
Roundtrip flight included
Boston (BOS) 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

Le Barthélemy Hotel & Spa

5 out of 5
Save 100% on your flight
Price was $6,703, price is now $5,444 per person
$5,444
per person
May 18 - May 24
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
$1,767 nightly
The price is $1,851 total per night
$1,851 total
Mar 18 - Mar 19
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
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 free airport shuttle. Relax with a drink at the poolside bar and enjoy free perks like full breakfast and valet parking.
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy
$3,665 nightly
The price is $3,848 total per night
$3,848 total
Apr 1 - Apr 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.
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.
Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
1 Rue du Toiny St. Barthelemy
$2,012 nightly
The price is $2,113 total per night
$2,113 total
Mar 6 - Mar 7
Total with taxes and fees
A full-service spa, 2 restaurants, and 2 outdoor pools are all featured at this luxury hotel. 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
Baie de Grand Cul de Sac St. Barthelemy
$2,926 nightly
The price is $3,058 total per night
$3,058 total
Mar 16 - Mar 17
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.
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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.

Popular places to visit

Lorient Beach showing a sandy beach and general coastal views

Lorient Beach

Why not spend a carefree afternoon at Lorient Beach during your travels in Quartier Lorient? You can enjoy the restaurants while in the area.

Lorient Beach
Contrasts.

Saline Beach

Why not spend a carefree afternoon at Saline Beach during your travels in Morne Rouge?

Saline Beach
The most beautiful place in the world

Grand Cul de Sac

Why not spend a carefree afternoon at Grand Cul de Sac during your travels in Anse du Grand Cul-de-Sac?

Grand Cul de Sac

Photos of local treasures

Browse Windward vacation photos for more inspiration

Contrasts.
Contrasts.
Great place to relax after completing the route from "Going am wilden Kaiser".
The near end of the beach. So beautiful, and in the off-season, wonderfully quiet.
The most beautiful place in the world

Frequently asked questions

How much are vacation packages to Windward?
With vacation packages on offer for only $3,224, 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.