Title: Leeward Vacations & Trips 2026 from CA $6,402 | 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.

![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 $6,402

per person

Mar 20 - Mar 27

found 1 day ago

Roundtrip flight included

Ottawa (YOW) to Gustavia (SBH)

9.8/10 Exceptional! (94 reviews)

Great location at St.Jean beach. Staff were very helpful and great to talk with. The rooms are very small we stayed in jungle room 3\. No view or patio in room just in hall outside of room. Free breakfast. Overpriced for what is offered. 40 euros for taxi into town. We rented a car for 1 day that’s all you need to see most of island.

Reviewed on Jan 22, 2026

![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 $14,665

per person

Apr 13 - Apr 20

found 21 hours 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

![Le Toiny Hôtel & Beach Club](https://images.trvl-media.com/lodging/1000000/530000/528500/528429/372f985f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Le Toiny Hôtel & Beach Club

CA $12,191

per person

Mar 9 - Mar 16

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Gustavia (SBH)

9.8/10 Exceptional! (44 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 Aug 4, 2025

![Hotel Barrière Le Carl Gustaf St Barth](https://images.trvl-media.com/lodging/39000000/38820000/38812000/38811961/dc57b858_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Barrière Le Carl Gustaf St Barth

Lurin

CA $11,443

per person

Apr 13 - Apr 20

found 21 hours ago

Roundtrip flight included

Montreal (YMQ) to Gustavia (SBH)

9.8/10 Exceptional! (26 reviews)

We absolutely loved the hotel! The staff is amazing, and very accommodating. We celebrated my husband's 40th birthday and they truly made it unforgettable.

Reviewed on Dec 14, 2025

![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 $10,246

per person

Mar 9 - Mar 16

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Gustavia (SBH)

9.6/10 Exceptional! (226 reviews)

Great rooms, service and amenities!

Reviewed on Jan 19, 2026

## 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

Feb 9 - Feb 10

includes taxes & fees

9.6/10 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=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=15980957&PinnedHotelID=15980957&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 $1,555

CA $1,633 total

Feb 11 - Feb 12

includes taxes & fees

9.8/10 Exceptional! (53 reviews)

If you’re looking for tranquility, elegance, and an authentic St. Barts escape, Le Rêve de Saint Barth is absolutely exceptional. A place you’ll want to return to again and again ✨

Reviewed on Jan 23, 2026

[](https://expedia.ca/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=88474775&PinnedHotelID=88474775&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 $2,735

CA $2,994 total

Mar 10 - Mar 11

includes taxes & fees

9.2/10 Wonderful! (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://expedia.ca/Hotel-Search?startDate=10%2F03%2F2026&endDate=11%2F03%2F2026&selected=1182278&PinnedHotelID=1182278&HadPinnedHotel=true&regionId=553248635975177495)

[See all 1,463 properties in Leeward](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%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

![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)

![Panoramic view of vibrant St. Martin ](https://mediaim.expedia.com/localexpert/413439/1889a377-cdfa-4a6e-bdf7-cb7a36cef979.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Edge Ferry Tickets to St. Barts

CA $136

per adult

**84%** of travellers recommend

[](https://expedia.ca/things-to-do/edge-ferry-tickets-to-st-barts.a413439.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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