A red boat on a sandy beach with a rocky hill in the background.

Book Windward Hotels

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Property class

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Windward hotels

1. Le Sereno

Le Sereno
5.0 star property
Grand Cul-de-Sac
9.6 out of 10, Exceptional, (62 reviews)
"Loved our time at this property! The staff was really warm and the location is so unique! "
United States
babi
Le Sereno

2. Oyster Bay Beach Resort

Oyster Bay Beach Resort
4.0 star property
Oyster Pond
8.8 out of 10, Excellent, (1,008 reviews)
"Loved everything about this resort seriously!!"
United States
Elgetta
The price is AU$299
includes taxes & fees
18 Aug - 19 Aug
Oyster Bay Beach Resort

3. JW Marriott St. Maarten Beach Resort & Spa

JW Marriott St. Maarten Beach Resort & Spa
5.0 star property
Oyster Pond
8.8 out of 10, Excellent, (373 reviews)
"Our second time here and the hotel and staff are still the best!"
Canada
Mark
The price is AU$566
includes taxes & fees
19 Aug - 20 Aug
JW Marriott St. Maarten Beach Resort & Spa

4. Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel
3.5 star property
Oyster Pond
9.2 out of 10, Wonderful, (1,001 reviews)
"The property was beautiful, clean and the staff was impeccable! They put a bottle of wine in my room on my birthday. The front desk was amazing and also the housekeepers."
United States
Heather Elaine
The price is AU$252
includes taxes & fees
1 Sept - 2 Sept
Princess Heights Luxury Boutique Condo Hotel

5. Christopher Hotel

Christopher Hotel
5.0 star property
Pointe Milou
9.6 out of 10, Exceptional, (258 reviews)
"The hotel is amazing along with the staff they cover everything you need for the trip from room and hotel service to reservations A Must stay"
United States
vincent
Christopher Hotel

6. Les Balcons d'Oyster Pond

Les Balcons d'Oyster Pond
Oyster Pond
9.6 out of 10, Exceptional, (152 reviews)
"Beautiful setting, clean room, beautiful view, nice kitchen, nice balcony, easy to drive to Grand Case, Anse Marcel."
Canada
Adrian
Les Balcons d'Oyster Pond

7. Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten
4.0 star property
Oyster Pond
8.8 out of 10, Excellent, (33 reviews)
"Large rooms with great ocean views! Helpful staff and good beach access!"
United States
Gavin
The price is AU$1,066
includes taxes & fees
16 Aug - 17 Aug
Dawn Beach Club Resort Sint Maarten

8. Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth
Grand Cul-de-Sac
9.8 out of 10, Exceptional, (74 reviews)
"Relaxing, beautiful, chic, helpful, good food."
United States
Nina
Rosewood Le Guanahani St Barth

9. GYP SEA Saint Barth

GYP SEA Saint Barth
5.0 star property
Colombier
9.8 out of 10, Exceptional, (102 reviews)
"Very nice property. Wonderful staff."
United States
Christina
GYP SEA Saint Barth

10. Pearl Beach Hotel

Pearl Beach Hotel
Saint-Jean
9.4 out of 10, Exceptional, (206 reviews)
"This boutique hotel is amazing!!! The hotel is on the beach and in walking distance to resturants ."
United States
Michael
The price is AU$926
includes taxes & fees
27 Aug - 28 Aug
Pearl Beach Hotel

11. Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club
5.0 star property
Toiny
9.8 out of 10, Exceptional, (54 reviews)
"Nice place to stay and the staff are very friendly"
United States
Keshia
Le Toiny Hôtel & Beach Club

12. Fouquet's Saint-Barth

Fouquet's Saint-Barth
5.0 star property
Lurin
9.8 out of 10, Exceptional, (37 reviews)
"The staff was the best. Seriously best service ever."
United States
Michael Kelly
Fouquet's Saint-Barth

13. Tropical Hotel St Barth

Tropical Hotel St Barth
5.0 star property
Saint-Jean
9.8 out of 10, Exceptional, (134 reviews)
"Extraordinary experience. Best possible service. Everybody made us feel truly welcome from the very first moment. The staff were absolutely charming, incredibly friendly, and always attentive to every little detail. The hotel itself is small, cosy, and full of charm, creating a very warm and personal atmosphere. We felt genuinely looked after throughout our stay. A truly exceptional experience that we would love to repeat."
Spain
Charles
Tropical Hotel St Barth

14. Amnios St Barth

Amnios St Barth
Grand Cul-de-Sac
9.6 out of 10, Exceptional, (129 reviews)
"We had a great experience in Saint "
United States
LILIBETH
Amnios St Barth

15. Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa
5.0 star property
Grand Cul-de-Sac
9.8 out of 10, Exceptional, (90 reviews)
"Everything there was amazing and the staff"
United States
Salvatore
The price is AU$2,837
includes taxes & fees
16 Aug - 17 Aug
Le Barthélemy Hotel & Spa

16. Lil' Home

Lil' Home
Devet
9.0 out of 10, Wonderful, (12 reviews)
"Clean, beautiful view, great communication but the pool was cold. "
United States
Edwin
Lil' Home

17. Hotel Manapany

Hotel Manapany
5.0 star property
Anse des Cayes
9.4 out of 10, Exceptional, (71 reviews)
"Lovely, “barefoot chic” hotel that is top class in all respects"
United Kingdom
Quintin
Hotel Manapany

18. Reve de Saint Barth

Reve de Saint Barth
Merlette
9.8 out of 10, Exceptional, (69 reviews)
"This place is a hidden gem, our host Ninon was always available to help and answer any questions. I would recommend this place to anyone visiting St Barths."
United States
Albert
Reve de Saint Barth

19. Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina
4.0 star property
Oyster Pond
9.2 out of 10, Wonderful, (119 reviews)
"The condo and property was clean and well decorated and maintained. We had an awesome stay and will return."
United States
Donna
Coral Beach Club Villas & Marina

20. Hotel Les Ondines Sur La Plage

Hotel Les Ondines Sur La Plage
Grand Cul-de-Sac
10.0 out of 10, Exceptional, (89 reviews)
"This was a wonderful stay, the attentive staff, cleanliness, breakfast and overall experience was just perfect! I would highly recommend this hotel & would gladly return!"
United States
claudia
Hotel Les Ondines Sur La Plage
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windward Hotel Reviews

Guide to exploring Windward

Top reasons to visit Windward

  • Stunning Beaches: Windward boasts beautiful surf beaches, perfect for sunbathing and water sports.
  • Outdoor Activities: Enjoy hiking scenic trails and catching waves at the local surf club.
  • Charming Shopping: Explore delightful shopping areas for unique souvenirs and local crafts.
  • Scenic Views: Marvel at the breathtaking ocean views and lush landscapes of the Koolau Mountains.
  • Diverse Accommodation: Choose from a range of lodging options, including hotels, bed & breakfasts, and scenic apartments.

Find great hotels in Windward

Discover the charm of Windward, St. Barthelemy, where a variety of accommodation options await you. Whether you're seeking the comfort of a hotel, the warmth of a bed & breakfast, or a scenic apartment, this area offers something for every traveller. Enjoy beachside relaxation, family-friendly amenities, and exciting adventure experiences, ensuring your stay is both memorable and enjoyable. Explore popular choices like Windward Passage Hotel and Windward House for a delightful getaway.

  • Christopher Hotel: At the Christopher Hotel, families and boutique enthusiasts will find a welcoming paradise. This 5-star hotel features uniquely designed decor and artworks that enhance its charm, making it ideal for a relaxing getaway. The hotel is pet-friendly, allowing furry companions to join in on the fun. Young guests are well catered for with amenities such as children’s bathrobes, slippers, and a dedicated pool. With a myriad of family-friendly services, Christopher Hotel promises an unforgettable experience for visitors of all ages.
  • Rosewood Le Guanahani St Barth: Embrace adventure and romance at Rosewood Le Guanahani St Barth. This stunning property is perfect for couples seeking a getaway filled with excitement and relaxation. Guests can indulge in a variety of adventure sports, including snorkelling and hiking, while enjoying breathtaking views from the poolside and ocean-view dining. The hotel offers exclusive romance packages that feature champagne service and soothing spa treatments, ensuring a memorable experience for any romantic occasion. For those wanting to unwind, the full spa services promise a serene escape.
  • Le Barthélemy Hotel & Spa: Luxury and family comfort converge at Le Barthélemy Hotel & Spa. This 5-star establishment caters to both business travellers and families, providing essential amenities like a playground and shared foosball table for kids. The hotel’s sophisticated design and top-tier services make it a perfect choice for those seeking an upscale atmosphere. Business amenities ensure a seamless work environment, while leisure options allow families to bond and create lasting memories together, all set against the enchanting backdrop of Windward.

Where to stay in Windward

Windward, St. Barthelemy, offers a perfect blend of stunning ocean views and tranquil beaches, ideal for a romantic getaway or a relaxing holiday. Explore the lush scenery of the Koolau Mountains, unwind on the pristine shores reminiscent of Long Beach Island, and indulge in the luxury of secluded spots that promise serenity. This enchanting region is perfect for those seeking a picturesque escape in an idyllic Caribbean setting.

  • Morne Criquet: Nestled in the Windward area, Morne Criquet is a charming village that offers a delightful blend of beachside relaxation and outdoor adventure. The village sees moderate seasonal visitor numbers, peaking from January to March, making it a perfect winter getaway. Visitors flock here for its stunning scenery and outdoor activities, with popular options including golf courses and resorts. The proximity to picturesque beaches, a serene bay, and a bustling marina makes Morne Criquet an ideal spot for those looking to unwind or indulge in a variety of water sports. Experience the local charm and natural beauty that this village has to offer.
  • Quartier Lorient: Located near Windward, Quartier Lorient is a vibrant village that attracts visitors seeking a mix of beach leisure and outdoor activities. With a similar seasonal flow of tourists peaking in the early months of the year, it's a fantastic destination for sun-seekers. The area is renowned for its beautiful beaches and a variety of water sports, as well as a selection of spas for ultimate relaxation. Local attractions such as the marina and harbour add to the charm, providing opportunities for exploration and leisure. Quartier Lorient truly embodies the spirit of island living.
  • Grande Saline: Grande Saline is a picturesque neighbourhood located around Windward, celebrated for its pristine beaches and breathtaking scenery. Visitors arrive in waves throughout the year, with the busiest months from January to March. The neighbourhood is well-known for its nudist beach, offering a unique experience for the adventurous traveller. Outdoor enthusiasts can enjoy golf courses and luxurious resorts that complement the stunning natural surroundings. Grande Saline's proximity to beautiful bays and serene beaches makes it a perfect retreat for both relaxation and exploration, ensuring a memorable holiday experience.

Things to do in Windward

Windward, St. Barthelemy, is perfect for beach lovers and outdoor enthusiasts. You can catch some waves at the local surf club or relax on the stunning surf beach. Avid hikers will enjoy exploring the scenic trails, while those looking to indulge in a bit of retail therapy can visit the charming shopping areas nearby. Whether you're after adventure or relaxation, Windward has something for everyone.

Booking tips and Expedia advantages for Windward

To save money on your trip to Windward, consider visiting during the off-peak months of July to September when prices drop. Booking your hotel about three months in advance can secure better rates, and Monday is the cheapest day to stay. Use Expedia’s tools to compare prices and refine your search based on your budget and accommodation type. Bundling your hotel stay with flights and activities can also lead to significant savings. Don't forget to check for last-minute deals for additional discounts!

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Windward are July to September, where the prices are slightly lower. This is in comparison to January to March, where prices are slightly higher.
  • The best time to book a hotel: Book your hotel in Windward about 3+ months out to secure some of the cheapest prices. If you're the spontaneous type, Expedia's last minute deals and discounts are indicated via the green label below the price.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Windward is Monday. The most expensive day to stay in Windward is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, such as your budget, preferred location, and the type of accommodation you’re after. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save some dollars by bundling your Windward hotel stay with your flights and activities through an Expedia package deal.

Best time to go to Windward

The best time to visit Windward can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windward falls in September and September. September has moderately low visitor numbers and mostly sunny weather. The coolest average temperature in Windward falls in March and March. March has moderately high visitor numbers and mostly sunny weather.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January78.3°F (25.700000000000003°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
January78.3°F (25.700000000000003°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
February77.7°F (25.4°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
February77.7°F (25.4°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
March77.5°F (25.3°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
March77.5°F (25.3°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
April78.6°F (25.9°C)No Rain (Dry)Mostly SunnyAverageAverage
April78.6°F (25.9°C)No Rain (Dry)Mostly SunnyAverageAverage
May80.1°F (26.700000000000003°C)Light RainMostly SunnyAverageAverage
May80.1°F (26.700000000000003°C)Light RainMostly SunnyAverageAverage
June81.5°F (27.5°C)Light RainMostly SunnyAverageAverage
June81.5°F (27.5°C)Light RainMostly SunnyAverageAverage
July82.0°F (27.8°C)Light RainMostly SunnyAverageSlightly Low
July82.0°F (27.8°C)Light RainMostly SunnyAverageSlightly Low
August82.6°F (28.1°C)Light RainMostly SunnyModerately LowSlightly Low
August82.6°F (28.1°C)Light RainMostly SunnyModerately LowSlightly Low
September82.9°F (28.3°C)Light RainMostly SunnyModerately LowSlightly Low
September82.9°F (28.3°C)Light RainMostly SunnyModerately LowSlightly Low
October82.4°F (28.0°C)Light RainMostly CloudyModerately LowAverage
October82.4°F (28.0°C)Light RainMostly CloudyModerately LowAverage
November81.1°F (27.3°C)Light RainMostly CloudyAverageAverage
November81.1°F (27.3°C)Light RainMostly CloudyAverageAverage
December79.5°F (26.4°C)No Rain (Dry)Mostly SunnyAverageAverage
December79.5°F (26.4°C)No Rain (Dry)Mostly SunnyAverageAverage