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
Price was $3,786, price is now $2,557 per person
$2,557
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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
Price was $4,034, price is now $2,662 per person
$2,662
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip 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 Toiny Hôtel & Beach Club
Save 100% on your flight
Price was $6,448, price is now $4,844 per person
$4,844
per person
Apr 4 - Apr 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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
Save 100% on your flight
Price was $4,969, price is now $4,019 per person
$4,019
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Christopher Hotel
Price was $5,416, price is now $4,468 per person
$4,468
per person
Apr 4 - Apr 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Gustavia (SBH)
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.
Top Windward hotels deals
Tropical Hotel St Barth
Les Hauts de Saint Jean St. Barthelemy
$1,151 nightly
The price is $1,209 total per night
$1,209 total
Feb 2 - Feb 3
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
Christopher Hotel
Pointe Milou, 9 St. Barthelemy
$1,795 nightly
The price is $1,879 total per night
$1,879 total
Feb 1 - Feb 2
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
Le Sereno
Grand Cul de Sac BP 19 St. Barthelemy
$2,204 nightly
The price is $2,314 total per night
$2,314 total
Jan 19 - Jan 20
Total with taxes and fees
This smoke-free hotel features a private beach, a full-service spa, and a restaurant. Dine at the beachfront restaurant and relax with beach umbrellas. Enjoy the outdoor pool and free perks like full breakfast and free self parking.
On private beach
Pool
Rosewood Le Guanahani St Barth
Grand Cul De Sac St. Barthelemy
This luxury hotel features a full-service spa, 2 outdoor pools, and a restaurant. Relax with a drink at one of the 2 bars/lounges 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
$2,891 nightly
The price is $3,023 total per night
$3,023 total
Feb 3 - Feb 4
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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Photos of local treasures
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