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
Save 100% on your flight
Price was $4,594, price is now $3,519 per person
$3,519
per person
Jan 29 - Feb 1
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.
Hotel Manapany
Anse des Cayes
Save 100% on your flight
Price was $8,611, price is now $5,157 per person
$5,157
per person
Feb 15 - Feb 21
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 $7,810, price is now $4,902 per person
$4,902
per person
Feb 15 - Feb 21
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
Save 100% on your flight
Price was $12,730, price is now $9,035 per person
$9,035
per person
Feb 18 - Feb 24
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.
GYP SEA Saint Barth
Save 100% on your flight
Price was $7,261, price is now $5,457 per person
$5,457
per person
Feb 15 - Feb 21
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
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
Christopher Hotel
Pointe Milou, 9 St. Barthelemy
$1,117 nightly
The price is $1,165 total per night
$1,165 total
Dec 17 - Dec 18
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 Barthélemy Hotel & Spa
Baie de Grand Cul de Sac St. Barthelemy
$2,569 nightly
The price is $2,683 total per night
$2,683 total
Dec 17 - Dec 18
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
Rosewood Le Guanahani St Barth
Grand Cul De Sac St. Barthelemy
$1,906 nightly
The price is $2,001 total per night
$2,001 total
Dec 8 - Dec 9
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
Le Sereno
Grand Cul de Sac BP 19 St. Barthelemy
$1,809 nightly
The price is $1,900 total per night
$1,900 total
Dec 11 - Dec 12
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
Le Toiny Hôtel & Beach Club
1 Rue du Toiny St. Barthelemy
$2,895 nightly
The price is $3,039 total per night
$3,039 total
Dec 19 - Dec 20
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
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
Gouverneur Beach
Why not spend a carefree afternoon at Gouverneur Beach during your travels in Anse du Gouverneur?
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?
Photos of local treasures
Browse Windward vacation photos for more inspiration
