--- title: "Windward Holidays 2026 | Expedia" description: "Book your ATOL protected Windward holiday today! Enjoy flexibility with our interest-free instalments & book now pay later option. Fully refundable rates on most hotels." canonical: "https://www.expedia.co.uk/Windward.d553248635975177497.Holidays-City-Breaks" language: en-GB market: GB currency: GBP prices_as_of: 2026-11-14T17:28:19Z --- ![A red boat on a sandy beach with a rocky hill in the background.](https://images.trvl-media.com/place/553248635975748157/ed061e98-6278-4fb2-bd10-fdc8edbedb0d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) Photo by Charles Guerrero # Windward Holidays ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £750 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. Trip length 3 nights4 nights5 nights6-7 nights Stars 5 star4 star & up3 star & up2 star & up Flight class EconomyPremium economyBusinessFirst class Remove all filters - ![A poolside area with lounge chairs and a view of the ocean and a hillside with buildings.](https://images.trvl-media.com/lodging/1000000/10000/7000/6956/00bf2ae6.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A balcony with wicker chairs and a view of the ocean and hills.](https://images.trvl-media.com/lodging/1000000/10000/7000/6956/949a123a.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **22 Dec - 26 Dec** ### [Tropical Hotel St Barth + Flight](https://www.expedia.co.uk/go/package/search/FlightHotel/2026-12-22/2026-12-26/?FromAirport=LON&Destination=SBH&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6956&dealMarker=&paandie=true&cabinClass=e) Saint-Jean 4 nights **9.8/10** \- Exceptional (135 reviews) Return • London (LON) - St. Barthelemy (SBH) LGW - SBH • 1 stop SBH - LGW • 1 stop [~~£4,518~~](https://www.expedia.co.uk/) **£3,695** per traveller found 1 day ago - ![A resort with a pool, beach, and boats in the water.](https://images.trvl-media.com/lodging/16000000/15990000/15981000/15980957/f8fa9554.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A rectangular pool surrounded by palm trees and lounge chairs, with a clear blue sky in the background.](https://images.trvl-media.com/lodging/16000000/15990000/15981000/15980957/fed66445.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **22 Dec - 26 Dec** ### [GYP SEA Saint Barth + Flight](https://www.expedia.co.uk/go/package/search/FlightHotel/2026-12-22/2026-12-26/?FromAirport=LON&Destination=SBH&NumRoom=1&NumAdult=2&NumChild=0&hotelId=15980957&dealMarker=&paandie=true&cabinClass=e) Colombier 4 nights **9.8/10** \- Exceptional (105 reviews) Return • London (LON) - St. Barthelemy (SBH) LGW - SBH • 1 stop SBH - LGW • 1 stop [~~£5,833~~](https://www.expedia.co.uk/) **£5,116** per traveller found 1 day ago - ![An infinity pool with a view of the ocean, outdoor dining area with tables and chairs, and palm trees.](https://images.trvl-media.com/lodging/1000000/530000/528500/528429/5d0b0ab5.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A covered outdoor seating area with a view of the ocean, bar with stools, and a poolside lounge.](https://images.trvl-media.com/lodging/1000000/530000/528500/528429/c912bed0.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **22 Dec - 26 Dec** ### [Le Toiny Hôtel & Beach Club + Flight](https://www.expedia.co.uk/go/package/search/FlightHotel/2026-12-22/2026-12-26/?FromAirport=LON&Destination=SBH&NumRoom=1&NumAdult=2&NumChild=0&hotelId=528429&dealMarker=&paandie=true&cabinClass=e) Toiny 4 nights **9.8/10** \- Exceptional (59 reviews) "My husband and I stayed here for our honeymoon and had the most beautiful villa! When we checked into our villa there was the most wonderful welcome gift and card. It was the perfect peaceful and quiet oasis to end our trip. We loved the shuttle that takes you down to their beach club and beach where you can have lunch and enjoy the ocean views. The beach was rocky so we didn’t swim, but there is a pool down by the beach as well. We absolutely loved that everything was Le Toiny branded. The..." Reviewed October 24, 2026 Return • London (LON) - St. Barthelemy (SBH) LGW - SBH • 1 stop SBH - LGW • 1 stop [~~£7,024~~](https://www.expedia.co.uk/) **£6,212** per traveller found 1 day ago ### What to do in Windward ![High-Speed Ferry to St. Barths](https://mediaim.expedia.com/localexpert/176989/803f204c-e59b-47d1-9a40-1a59056c3ffb.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [High-Speed Ferry to St. Barths](https://www.expedia.co.uk/things-to-do/a.a176989.activity-details?rid=553248635975177497) £61 per adult 78% of travellers recommend ![Full-Day St Barth Private Charter Tour](https://mediaim.expedia.com/localexpert/44922206/f865c94a-c92d-49a3-a084-520484d4378d.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [Full-Day St Barth Private Charter Tour](https://www.expedia.co.uk/things-to-do/a.a44922206.activity-details?rid=553248635975177497) £1,426 per traveller 0% of travellers recommend [See all activities in Windward](https://www.expedia.co.uk/things-to-do/search?rid=553248635975177497) ## Windward Hotel Deals ### [Christopher Hotel](https://www.expedia.co.uk/St-Barthelemy-Hotels-Christopher-Hotel.h9481.Hotel-Information) ![A poolside area with lounge chairs and umbrellas, a person in a white robe, and a view of the sea and hills in the background.](https://images.trvl-media.com/lodging/1000000/10000/9500/9481/96a64866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Pointe Milou, 9, St. Barthelemy, 97133, BL - Location: 1.1 mi from Windward - Star rating: 5/5 - Guest rating: 9.6/10 (Exceptional, 266 reviews) - Price: £1,053, includes taxes & fees, 29 Nov - 30 Nov ### [Hotel Les Ondines Sur La Plage](https://www.expedia.co.uk/St-Barthelemy-Hotels-Hotel-Les-Ondines-Sur-La-Plage.h10658309.Hotel-Information) ![A beachside resort with thatched umbrellas, lounge chairs, and a view of the ocean and distant hills.](https://images.trvl-media.com/lodging/11000000/10660000/10658400/10658309/a3c346b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Grand Cul De Sac Plage, St. Barthelemy, 97133, BL - Location: 1.2 mi from Windward - Guest rating: 10/10 (Exceptional, 91 reviews) - Price: £601, includes taxes & fees, 23 Nov - 24 Nov ### [Tropical Hotel St Barth](https://www.expedia.co.uk/St-Barthelemy-Hotels-Tropical-Hotel-St-Barth.h6956.Hotel-Information) ![A poolside area with lounge chairs and a view of the ocean and a hillside with buildings.](https://images.trvl-media.com/lodging/1000000/10000/7000/6956/00bf2ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Les Hauts de Saint Jean, St. Barthelemy, 97133, BL - Location: 1.1 mi from Windward - Star rating: 5/5 - Guest rating: 9.8/10 (Exceptional, 135 reviews) - Price: £689, includes taxes & fees, 16 Nov - 17 Nov ### [Le Toiny Hôtel & Beach Club](https://www.expedia.co.uk/St-Barthelemy-Hotels-Hotel-Le-Toiny.h528429.Hotel-Information) ![An infinity pool with a view of the ocean, outdoor dining area with tables and chairs, and palm trees.](https://images.trvl-media.com/lodging/1000000/530000/528500/528429/5d0b0ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1 Rue du Toiny, St. Barthelemy, 97133, BL - Location: 1.3 mi from Windward - Star rating: 5/5 - Guest rating: 9.8/10 (Exceptional, 59 reviews) - Price: £1,378, includes taxes & fees, 13 Dec - 14 Dec - Review: "My husband and I stayed here for our honeymoon and had the most beautiful villa! When we checked into our villa there was the most wonderful welcome gift and card. It was the perfect peaceful and quiet oasis to end our trip. We loved the shuttle that takes you down to their beach club and beach where you can have lunch and enjoy the ocean views. The beach was rocky so we didn’t swim, but there is a pool down by the beach as well. We absolutely loved that everything was Le Toiny branded. The... ### [Le Barthélemy Hotel & Spa](https://www.expedia.co.uk/St-Barthelemy-Hotels-Le-Barthelemy-Hotel-Spa.h14909517.Hotel-Information) ![A clear blue pool with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.](https://images.trvl-media.com/lodging/15000000/14910000/14909600/14909517/b890f3c5_edited_0e1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Baie de Grand Cul de Sac, St. Barthelemy, 97133, BL - Location: 1.2 mi from Windward - Star rating: 5/5 - Guest rating: 9.8/10 (Exceptional, 92 reviews) - Price: £2,083, includes taxes & fees, 16 Nov - 17 Nov - Review: One of the best hotels that I stayed with my wife in the Caribbean. ### [GYP SEA Saint Barth](https://www.expedia.co.uk/St-Barthelemy-Hotels-Hotel-Villa-Marie-Saint-Barth.h15980957.Hotel-Information) ![A resort with a pool, beach, and boats in the water.](https://images.trvl-media.com/lodging/16000000/15990000/15981000/15980957/f8fa9554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Le Colombier, St. Barthelemy, 97133, BL - Location: 3.2 mi from Windward - Star rating: 5/5 - Guest rating: 9.8/10 (Exceptional, 105 reviews) - Price: £820, includes taxes & fees, 16 Nov - 17 Nov - Review: Excellent service!! ### [Fouquet's Saint-Barth](https://www.expedia.co.uk/St-Barthelemy-Hotels-Hotel-Barriere-Le-Carl-Gustaf-St-Barth.h38811961.Hotel-Information) ![A beach with rows of sun loungers under umbrellas, a rocky cliff in the background, and a clear blue sea.](https://images.trvl-media.com/lodging/39000000/38820000/38812000/38811961/c683c46c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Rue des Normands, Lieu Dit Lurin, St. Barthelemy, Leeward, 97133, BL - Location: 2 mi from Windward - Star rating: 5/5 - Guest rating: 9.6/10 (Exceptional, 38 reviews) - Price: £1,664, includes taxes & fees, 1 Dec - 2 Dec - Review: Amazing hotel with wonderful staff. ### [Hotel Manapany](https://www.expedia.co.uk/St-Barthelemy-Hotels-Hotel-Manapany.h1182278.Hotel-Information) ![A poolside view with a clear blue ocean, palm trees, and a mountainous backdrop.](https://images.trvl-media.com/lodging/2000000/1190000/1182300/1182278/fde4e022.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Anse des Cayes, St. Barthelemy, 97133, BL - Location: 2 mi from Windward - Star rating: 5/5 - Guest rating: 9.4/10 (Exceptional, 71 reviews) - Price: £856, includes taxes & fees, 16 Nov - 17 Nov - Review: Lovely, “barefoot chic” hotel that is top class in all respects 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. [See all properties in Windward](https://www.expedia.co.uk/Hotel-Search?startDate=2026-11-28&endDate=2026-11-29®ionId=553248635975177497&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Frequently Asked Questions ### How much does a Windward travel package cost? Starting from as low as £3,695, 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](https://www.expedia.co.uk/service/?langid=1033) 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. \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ## Other language versions ```yaml hreflang: x-default: https://www.expedia.com/ fr-FR: https://www.expedia.fr/Windward.d553248635975177497.Reservation-Sejours-Voyages ```