Title: Leeward Vacations & Trips 2026 from CA $5,571 | Expedia.ca

[Leeward Hotels](https://expedia.ca/Destinations-In-Leeward.d553248635975177495.Hotel-Destinations)[Vacation Rentals in Leeward](https://expedia.ca/Destinations-In-Leeward.d553248635975177495.Vacation-Rental-Destinations)[Leeward Car Rentals](https://expedia.ca/Destinations-In-Leeward.d553248635975177495.Car-Rental-Destinations)

![](https://images.trvl-media.com/place/10758/05e0490b-441b-41b9-9404-0243de3354e0.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Leeward Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

Photo by Charles Guerrero

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 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  
Plan, book, and manage your trip all in one place

## Top Leeward Vacation Deals

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

![Christopher Hotel](https://images.trvl-media.com/lodging/1000000/10000/9500/9481/4be4cba9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Christopher Hotel

CA $5,571

per person

May 16 - May 23

found 12 hours ago

Roundtrip flight included

Toronto (YTO) to Gustavia (SBH)

9.6/10 Exceptional! (226 reviews)

Great rooms, service and amenities!

Reviewed on Jan 19, 2026

![Tropical Hotel St Barth](https://images.trvl-media.com/lodging/1000000/10000/7000/6956/c0efe738_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Tropical Hotel St Barth

CA $6,367

per person

Mar 26 - Mar 30

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Gustavia (SBH)

9.8/10 Exceptional! (94 reviews)

The service was excellent - especially the concierge. The staff was friendly and always accommodating. The hotel was beautiful; room was spotless and comfortable. We enjoyed the breakfast thoroughly! Would recommend to everyone!

Reviewed on Feb 12, 2026

![GYP SEA Saint Barth](https://images.trvl-media.com/lodging/16000000/15990000/15981000/15980957/355efd8e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### GYP SEA Saint Barth

CA $6,156

per person

Mar 26 - Mar 30

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Gustavia (SBH)

9.8/10 Exceptional! (83 reviews)

Great service Amazing beach club

Reviewed on Nov 24, 2025

![Le Barthélemy Hotel & Spa](https://images.trvl-media.com/lodging/15000000/14910000/14909600/14909517/291e5741_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Le Barthélemy Hotel & Spa

CA $9,585

per person

Mar 26 - Mar 30

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Gustavia (SBH)

9.8/10 Exceptional! (77 reviews)

Staff-10/10 Food-10/10 Amenities-10/10 Only thing Le Barthelemy - wish they use cooling bedsheets. Or comforters - that are less warm.

Reviewed on Dec 15, 2025

![Hotel Manapany](https://images.trvl-media.com/lodging/2000000/1190000/1182300/1182278/c2c871fc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Manapany

Anse des Cayes

CA $6,811

per person

Mar 26 - Mar 30

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Gustavia (SBH)

9.4/10 Exceptional! (66 reviews)

The property was exquisite. The entire staff was incredible, especially Noémie from Reception. She went above and beyond to make our 11th anniversary very memorable. I am already looking forward to a more extended visit to Hotel Manapany.

Reviewed on Jun 15, 2025

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_553248635975177495)

## Leeward Hotel Deals

![GYP SEA Saint Barth](https://images.trvl-media.com/lodging/16000000/15990000/15981000/15980957/355efd8e_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

GYP SEA Saint Barth

Le Colombier St. Barthelemy 

CA $1,705

CA $1,791 total

Mar 1 - Mar 2

includes taxes & fees

9.8/10 Exceptional! (89 reviews)

Beautiful property, good food. Loved the decor. Having dedicated beach chairs at Gyp sea Beach club was a huge plus. The best beach in my opinion! Staff was so friendly and responsive. Would definitely stay here again.

Reviewed on Jan 24, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=15980957&PinnedHotelID=15980957&HadPinnedHotel=true&regionId=553248635975177495)

![Hotel Manapany](https://images.trvl-media.com/lodging/2000000/1190000/1182300/1182278/c2c871fc_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel Manapany

Anse des Cayes St. Barthelemy 

CA $2,310

CA $2,523 total

Mar 9 - Mar 10

includes taxes & fees

[](https://expedia.ca/Hotel-Search?startDate=09%2F03%2F2026&endDate=10%2F03%2F2026&selected=1182278&PinnedHotelID=1182278&HadPinnedHotel=true&regionId=553248635975177495)

![Reve de Saint Barth](https://images.trvl-media.com/lodging/89000000/88480000/88474800/88474775/57f48ebb_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Reve de Saint Barth

Les Hauts de Flamands, Merlette St. Barthelemy 

CA $1,413

CA $1,483 total

Feb 26 - Feb 27

includes taxes & fees

9.8/10 Exceptional! (55 reviews)

The cleanliness of the unit was quite disappointing.

Reviewed on Feb 4, 2026

[](https://expedia.ca/Hotel-Search?startDate=26%2F02%2F2026&endDate=27%2F02%2F2026&selected=88474775&PinnedHotelID=88474775&HadPinnedHotel=true&regionId=553248635975177495)

[See all 1,454 properties in Leeward](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F02%2F2026&endDate=26%2F02%2F2026&regionId=553248635975177495)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does a Leeward vacation package cost?

### How do I get a cheap travel package to Leeward?

### How far in advance should I book my Leeward vacation?

### What does an Expedia Leeward travel package include?

### What should I know before booking a Leeward travel package?

### Can I choose my airline with a Leeward Expedia vacation package?

### If I'm not able to travel, can I cancel my Leeward vacation package?

### What to do in Leeward

![Sightseeing Tour of the French and Dutch Sides of the Island](https://mediaim.expedia.com/localexpert/686653/404621fb-5f43-421e-bffb-058e0a0058ce.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island

CA $76

per adult

**92%** of travellers recommend

[](https://expedia.ca/things-to-do/st-martin-and-st-maarten-sightseeing-tour-of-the-french-and-dutch-sides-of-the-island.a686653.activity-details)

![Amazing Plane Spotting at Maho Beach](https://mediaim.expedia.com/localexpert/1705818/7671bf3b-23be-4c78-aa80-df73918c3465.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Amazing Plane Spotting at Maho Beach

CA $36

per adult

[](https://expedia.ca/things-to-do/amazing-plane-spotting-at-maho-beach.a1705818.activity-details)

![Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line](https://mediaim.expedia.com/localexpert/466226/f1e62739-a072-49a6-976a-ce1a3facd837.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

CA $184

per adult

**90%** of travellers recommend

[](https://expedia.ca/things-to-do/sky-explorer-flying-dutchman-schooner-sentry-hill-line.a466226.activity-details)

[See all activities in Leeward](https://expedia.ca/things-to-do/search?rid=553248635975177495)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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## Go further with the Expedia app

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