Windward Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Charles Guerrero

  • Plan, book, travel with confidence

  • Better together

    Save up to £250 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Top Windward Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou
Price was £4,195, price is now £3,599 per person
£3,599
per person
6 Jun - 13 Jun
found 6 hours ago
Return direct flight included
London (LGW) to Gustavia (SBH)
9.6/10 Exceptional! (235 reviews)
Excellent service with a great location. Gladly return to this hotel.

Reviewed on 14 Mar 2026

Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
Price was £6,677, price is now £5,061 per person
£5,061
per person
6 Jun - 13 Jun
found 6 hours ago
Return direct flight included
London (LGW) to Gustavia (SBH)
9.8/10 Exceptional! (48 reviews)
It was perfect . It’s a beautiful property and the service was a dream. They thought about and catered to everything proactively.

Reviewed on 4 Aug 2025

Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Price was £5,590, price is now £4,343 per person
£4,343
per person
6 Jun - 13 Jun
found 6 hours ago
Return direct flight included
London (LGW) to Gustavia (SBH)
9.4/10 Exceptional! (70 reviews)
365 degrees of beauty the eye wanders off to more and more beauty! The staff is excellent, kind and so so lovely! The concierge took care of our every need! We’re definitely going to stay again!

Reviewed on 16 Mar 2026

Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Saint-Jean
Price was £4,794, price is now £3,929 per person
£3,929
per person
26 May - 3 Jun
found 1 day ago
Return direct flight included
London (LON) to Gustavia (SBH)
9.8/10 Exceptional! (107 reviews)
immaculate all around

Reviewed on 5 Apr 2026

GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Colombier
Price was £4,300, price is now £3,666 per person
£3,666
per person
6 Jun - 13 Jun
found 6 hours ago
Return direct flight included
London (LGW) to Gustavia (SBH)
9.8/10 Exceptional! (93 reviews)
Amazing experience 5 stars

Reviewed on 2 Mar 2026

Windward Essential Information

Language
French
Currency
Euros
Local Welcome
Salut / Bonjour
Local Goodbye
Au revoir / À bientôt
Closest Airport
Gustaf III Airport (SBH)

Top hotels in Windward

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
The price is £728 per night from 17 May to 18 May
£728
17 May - 18 May
includes taxes & fees
9.6/10 Exceptional! (236 reviews)
Staff super friendly. Pool could be a touch warmer

Reviewed on 7 Apr 2026

Christopher Hotel
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Baie de Grand Cul de Sac St. Barthelemy
The price is £1,414 per night from 20 May to 21 May
£1,414
20 May - 21 May
includes taxes & fees
9.8/10 Exceptional! (87 reviews)
We had a fabulous stay from start to finish. All the staff were welcoming and attentive and the concierge service was super helpful with recommendations and organizing bookings for restaurants. The hotel had great amenities including the spa, and our beachfront suite was wonderful. Being able to ...

Reviewed on 6 Apr 2026

Le Barthélemy Hotel & Spa
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
The price is £559 per night from 25 May to 26 May
£559
25 May - 26 May
includes taxes & fees
9.8/10 Exceptional! (107 reviews)
immaculate all around

Reviewed on 5 Apr 2026

Tropical Hotel St Barth
See all 2,352 properties in Windward
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Windward travel package cost?
Starting from as low as £3,599, you can create your own Windward travel package. Simply bundle flights, hotels and car rentals and we'll reward you with discounts.
If I'm not able to travel, can I cancel my Windward travel package?
It's impossible to predict what the future holds, so it's comforting to know that you can cancel or change your Windward travel package. If your booking was made in the last 24 hours, you may be entitled to a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.
How do I get a cheap travel package to Windward?
Combine your bookings with Expedia to save big on your next exciting adventure. With more than 550 airlines and 1,000,000 hotels worldwide, your Windward holiday package can be tailored exactly to suit your travel style. With all that extra money, why not add a few exciting tours and experiences? It's an easy way to unlock even more bargains. That holiday you've always dreamed of in Windward is much closer than you thought!
Does Expedia offer Book Now, Pay Later Windward holidays?
Expedia has joined forces with online lender Klarna to make your next trip easier on your wallet. Paying in instalments means you can spread the costs of your next dream escape, leaving you with more money to play with while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that fits your budget. Check out these flexible payment options:

  • Pay monthly holidays: Klarna has easy monthly payment plans that fit all budgets, so you can escape on that well-earned holiday now.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then select this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to click that "book now" button, opt for a low deposit holiday payment plan with Klarna.

How far in advance should I book my Windward holiday?
It can be hard to know exactly when the best time is to book your Windward holiday. But generally the earlier you book, the better the prices. Sometimes, you can reserve your flights and hotels up to 12 months before departure. If you're considering a last-minute getaway, no need to worry! There are fabulous bargains advertised on Expedia every single day.
What does an Expedia Windward travel package include?
Expedia has all you need to arrange your Windward trip, but how you structure your package is your call. Select from any combination of rental cars, hotels and flights. Chasing some activities or tours to keep you on the go? Once you've made your booking, you can add them on too. No matter your budget, there's a package deal to meet your needs.
What should I know before booking a Windward travel package?
When you book your hotels, flights and car rentals together, you'll pick up great discounts. Whether you're organising a rural escape in a cottage or would rather stay in a ritzy city hotel, Expedia can make it happen for less.
Can I choose my airline with a Windward Expedia travel package?
Yes, the choice is all yours. Expedia has access to more than 550 partner airlines throughout the world, so you can tailor your Windward holiday according to your style and budget.

Popular places to visit

Gouverneur Beach

Gouverneur Beach

Why not spend a care-free afternoon at Gouverneur Beach during your travels in Anse du Gouverneur?

Gouverneur Beach

What to do in Windward

Love Boat

Full-Day St Barth Private Charter Tour

£1,479
per traveller
Full-Day St Barth Private Charter Tour
See all activities in Windward

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.