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 $4,863, price is now $3,223 per person
$3,223
per person
Jan 8 - Jan 13
found 9 hours ago
Roundtrip non-stop 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
Save 100% on your flight
Price was $6,882, price is now $4,687 per person
$4,687
per person
Jan 8 - Jan 13
found 9 hours ago
Roundtrip non-stop 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 $51,526, price is now $36,704 per person
$36,704
per person
Dec 27 - Jan 3
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 $6,628, price is now $4,791 per person
$4,791
per person
Jan 8 - Jan 13
found 9 hours 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
Save 100% on your flight
Price was $6,507, price is now $5,185 per person
$5,185
per person
Jan 8 - Jan 13
found 9 hours 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
Christopher Hotel
Pointe Milou, 9, St. Barthelemy
$1,052 nightly
The price is $1,095 total per night
$1,095 total
Nov 2 - Nov 3
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
Rosewood Le Guanahani St Barth
Grand Cul De Sac, St. Barthelemy
$998 nightly
The price is $1,048 total per night
$1,048 total
Oct 23 - Oct 24
Total with taxes and fees
This award-winning 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
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
Le Barthélemy Hotel & Spa
Baie de Grand Cul de Sac, St. Barthelemy
$1,446 nightly
The price is $1,504 total per night
$1,504 total
Oct 23 - Oct 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
Le Toiny Hôtel & Beach Club
1 Rue du Toiny, St. Barthelemy
$986 nightly
The price is $1,035 total per night
$1,035 total
Oct 16 - Oct 17
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
Hotel Villa Lodge 4 épices
Lagon de Grand-Cul-de Sac, St. Barthelemy
A restaurant and an outdoor pool are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas and free airport shuttle. Guests will appreciate freebies like continental breakfast and free self 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
Why not spend a carefree afternoon at Lorient Beach during your travels in Quartier Lorient? You can enjoy the restaurants while in the area.
Gouverneur Beach
Why not spend a carefree afternoon at Gouverneur Beach during your travels in Anse du Gouverneur?
Saline Beach
Why not spend a carefree afternoon at Saline Beach during your travels in Morne Rouge?
Photos of local treasures
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