Deals on vacations and trips to Windward
Save when you book Windward package deals
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
$1,582 nightly
The price is $1,661 total per night
$1,661 total
Mar 26 - Mar 27
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
$2,612 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.
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