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.
Fouquet's Saint-Barth
Lurin
Save 100% on your flight
Price was $7,810, price is now $5,667 per person
$5,667
per person
May 15 - May 20
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.
Le Toiny Hôtel & Beach Club
Save 100% on your flight
Price was $6,776, price is now $5,167 per person
$5,167
per person
May 15 - May 20
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.
Christopher Hotel
Save 100% on your flight
Price was $3,022, price is now $2,425 per person
$2,425
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 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
$1,767 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.
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.
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.
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.
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 22 - Mar 23
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.
Le Sereno
Grand Cul de Sac BP 19 St. Barthelemy
$2,206 nightly
The price is $2,316 total per night
$2,316 total
Mar 6 - Mar 7
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
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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