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
Anse des Cayes
Save 100% on your flight
Price was $2,858, price is now $2,285 per person
$2,285
per person
Apr 23 - Apr 26
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
Price was $4,800, price is now $3,521 per person
$3,521
per person
Apr 12 - Apr 17
found 1 day 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
Price was $8,180, price is now $6,693 per person
$6,693
per person
Apr 12 - Apr 17
found 1 day ago
Roundtrip non-stop 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.
Fouquet's Saint-Barth
Lurin
Price was $5,600, price is now $4,765 per person
$4,765
per person
May 28 - Jun 2
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Gustavia (SBH)
A full-service spa, 2 restaurants, and a 24-hour gym 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.
GYP SEA Saint Barth
Price was $4,102, price is now $3,546 per person
$3,546
per person
Apr 12 - Apr 17
found 1 day ago
Roundtrip non-stop 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.
Top Windward hotels deals
Christopher Hotel
Pointe Milou, 9 St. Barthelemy
$1,223 nightly
The price is $1,279 total per night
$1,279 total
Apr 6 - Apr 7
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
Les Hauts de Saint Jean St. Barthelemy
$2,832 nightly
The price is $2,974 total per night
$2,974 total
Mar 20 - Mar 21
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
Rosewood Le Guanahani St Barth
Grand Cul De Sac St. Barthelemy
$2,592 nightly
The price is $2,721 total per night
$2,721 total
Apr 6 - Apr 7
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
Baie de Grand Cul de Sac St. Barthelemy
$2,666 nightly
The price is $2,785 total per night
$2,785 total
Apr 13 - Apr 14
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
Amnios St Barth
Lagon de Grand-Cul-de Sac St. Barthelemy
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 Toiny Hôtel & Beach Club
1 Rue du Toiny St. Barthelemy
$3,425 nightly
The price is $3,596 total per night
$3,596 total
Mar 26 - Mar 27
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.
Pool
Breakfast included
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
4/5(21 reviews)
Why not spend a carefree afternoon at Lorient Beach during your travels in Quartier Lorient? You can enjoy the restaurants while in the area.
Grand Cul de Sac
4/5(55 reviews)
Why not spend a carefree afternoon at Grand Cul de Sac during your travels in Anse du Grand Cul-de-Sac?
Saline Beach
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Why not spend a carefree afternoon at Saline Beach during your travels in Morne Rouge?
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