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
Save 100% on your flight
Price was $2,949, price is now $1,883 per person
$1,883
per person
May 6 - May 11
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.
Hotel Manapany
Anse des Cayes
Save 100% on your flight
Price was $6,071, price is now $4,088 per person
$4,088
per person
May 6 - May 13
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.
Le Toiny Hôtel & Beach Club
Save 100% on your flight
Price was $6,097, price is now $4,190 per person
$4,190
per person
May 6 - May 11
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
Save 100% on your flight
Price was $5,412, price is now $3,756 per person
$3,756
per person
May 6 - May 11
found 1 day ago
Roundtrip non-stop 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
Save 100% on your flight
Price was $2,798, price is now $2,160 per person
$2,160
per person
May 6 - May 11
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
$1,767 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
Les Hauts de Saint Jean 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 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
$2,612 nightly
The price is $2,743 total per night
$2,743 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.
Pool
Breakfast included
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
$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.
Pool
Breakfast included
Le Barthélemy Hotel & Spa
Baie de Grand Cul de Sac St. Barthelemy
$2,920 nightly
The price is $3,051 total per night
$3,051 total
Mar 23 - Mar 24
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
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
Why not spend a carefree afternoon at Lorient Beach during your travels in Quartier Lorient? You can enjoy the restaurants while in the area.
Saline Beach
Why not spend a carefree afternoon at Saline Beach during your travels in Morne Rouge?
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?
Photos of local treasures
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