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.
Christopher Hotel
Price was $2,514, price is now $2,141 per person
$2,141
per person
Oct 24 - Oct 27
found 14 hours ago
Roundtrip flight included
Boston (BOS) 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.
GYP SEA Saint Barth
Save 100% on your flight
Price was $7,259, price is now $5,285 per person
$5,285
per person
Oct 24 - Oct 28
found 14 hours ago
Roundtrip 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.
Hotel Manapany
Anse des Cayes
Save 100% on your flight
Price was $3,851, price is now $2,574 per person
$2,574
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip non-stop 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
Save 100% on your flight
Price was $3,412, price is now $2,417 per person
$2,417
per person
Nov 4 - Nov 7
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 $3,447, price is now $2,588 per person
$2,588
per person
Nov 4 - Nov 7
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.
Top Windward hotels deals
Christopher Hotel
Pointe Milou, 9, St. Barthelemy
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
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
Le Barthélemy Hotel & Spa
Baie de Grand Cul de Sac, St. Barthelemy
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
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. Free perks include continental breakfast, free self parking, and a roundtrip airport shuttle. Free WiFi in public areas, a terrace, and a garden are also on offer.
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.
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4.5/5(29 reviews)
Why not spend a carefree afternoon at Gouverneur Beach during your travels in Anse du Gouverneur?
Saline Beach
4.5/5(68 reviews)
Why not spend a carefree afternoon at Saline Beach during your travels in Morne Rouge?
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