Title: Leeward Vacation Packages 2026 from $1,883 | Expedia.com

[Leeward Travel Guide](https://expedia.com/Leeward.dx553248635975177495)[Leeward Hotels](https://expedia.com/Destinations-In-Leeward.d553248635975177495.Hotel-Destinations)[Vacation Rentals in Leeward](https://expedia.com/Destinations-In-Leeward.d553248635975177495.Vacation-Rental-Destinations)[Car Rentals in Leeward](https://expedia.com/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 Vacations & Trips from $1,883

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

Photo by Charles Guerrero

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to $1,045 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

## The Latest Leeward Vacation Packages

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

![Tropical Hotel St Barth](https://images.trvl-media.com/lodging/1000000/10000/7000/6956/00bf2ae6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Tropical Hotel St Barth

Save 100% on your flight

$1,883

per person

May 6 - May 11

found 7 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Gustavia (SBH)

9.8/10 Exceptional! (103 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

![Hotel Manapany](https://images.trvl-media.com/lodging/2000000/1190000/1182300/1182278/1e7d33e0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Manapany

Anse des Cayes

$4,247

per person

Apr 5 - Apr 10

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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

![Le Toiny Hôtel & Beach Club](https://images.trvl-media.com/lodging/1000000/530000/528500/528429/6d1e834e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Le Toiny Hôtel & Beach Club

$6,022

per person

Apr 5 - Apr 10

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Gustavia (SBH)

9.8/10 Exceptional! (46 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

![Le Barthélemy Hotel & Spa](https://images.trvl-media.com/lodging/15000000/14910000/14909600/14909517/b890f3c5_edited_0e1f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Le Barthélemy Hotel & Spa

Save 100% on your flight

$4,335

per person

May 6 - May 11

found 7 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Gustavia (SBH)

9.8/10 Exceptional! (84 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

![GYP SEA Saint Barth](https://images.trvl-media.com/lodging/16000000/15990000/15981000/15980957/f8fa9554_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### GYP SEA Saint Barth

$2,454

per person

May 21 - May 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Gustavia (SBH)

9.8/10 Exceptional! (90 reviews)

Amazing experience 5 stars

Reviewed on Mar 2, 2026

![](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.com/deals?rfrr=PKG_SPRING_PROMO_553248635975177495)

## Find the Best Leeward Vacation Packages

## Leeward Essential Information

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

## Leeward Hotel Deals

![GYP SEA Saint Barth](https://images.trvl-media.com/lodging/16000000/15990000/15981000/15980957/f8fa9554_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

GYP SEA Saint Barth

Le Colombier St. Barthelemy 

$1,173 nightly

$1,232 total

Apr 3 - Apr 4

Total with taxes and fees

9.8/10 Exceptional! (91 reviews)

Amazing experience 5 stars

Reviewed on Mar 2, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F3%2F2026&endDate=4%2F4%2F2026&selected=15980957&PinnedHotelID=15980957&HadPinnedHotel=true&regionId=553248635975177495)

![Hotel Manapany](https://images.trvl-media.com/lodging/2000000/1190000/1182300/1182278/1e7d33e0_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel Manapany

Anse des Cayes St. Barthelemy 

$1,865 nightly

$1,959 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://expedia.com/Hotel-Search?startDate=3%2F10%2F2026&endDate=3%2F11%2F2026&selected=1182278&PinnedHotelID=1182278&HadPinnedHotel=true&regionId=553248635975177495)

![Reve de Saint Barth](https://images.trvl-media.com/lodging/89000000/88480000/88474800/88474775/w7360h4910x0y0-825faa3a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Reve de Saint Barth

Les Hauts de Flamands, Merlette St. Barthelemy 

9.8/10 Exceptional! (56 reviews)

Great setup, the lady waited for me a while and i think its a hidden gem of St Barth for those who are mainly exploring.

Reviewed on Feb 24, 2026

[Get rates](https://expedia.com/Hotel-Search?startDate=3%2F18%2F2026&endDate=3%2F19%2F2026&selected=88474775&PinnedHotelID=88474775&HadPinnedHotel=true&regionId=553248635975177495)

[](https://expedia.com/Hotel-Search?startDate=3%2F18%2F2026&endDate=3%2F19%2F2026&selected=88474775&PinnedHotelID=88474775&HadPinnedHotel=true&regionId=553248635975177495)

[See all 1,284 properties in Leeward](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F5%2F2026&endDate=3%2F6%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.com/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.com/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)

Kid Friendly Vacations

[](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.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.com/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.com/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.com/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.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

LGBTQ Friendly Vacations

[](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adventure Vacations

[](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click)

![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Where to go when

[](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Honeymoon Vacations

[](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Mountain Vacations

[](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Fishing Vacations

[](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adults Only Vacations

[](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Waterpark Vacations

[](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Scuba Diving Vacations

[](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Yoga Vacations

[](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Cheap Vacations

[](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Solo Vacations

[](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click)

### Discover the most popular places to visit in Leeward

![Flamands Beach featuring rocky coastline, a sandy beach and general coastal views](https://images.trvl-media.com/place/6121004/dbef8c21-ffeb-4295-8728-a7dfe3fd238d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Flamands Beach

4.5/5(6 reviews)

Why not spend a carefree afternoon at Flamands Beach during your travels in Gustavia? Discover the area's museums and shops. 

[](https://expedia.com/Flamands-Beach-St-Barthelemy.d6121004.Vacation-Attraction)

![Colombier Beach which includes landscape views, a bay or harbor and general coastal views](https://images.trvl-media.com/place/6121000/9df45a5c-5f33-41c8-9067-ae5451e67312.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Colombier Beach

4.5/5(5 reviews)

If a restful vacation is part of your travel plans, Colombier Beach might be the perfect place to seek out during your trip to Colombier. 

[](https://expedia.com/Colombier-Beach-St-Barthelemy.d6121000.Vacation-Attraction)

#### Le P’tit Collectionneur

You can spend an afternoon studying the exhibits at Le P’tit Collectionneur during your travels in Gustavia. Stroll along the beaches or visit the spas in this romantic area. 

[](https://expedia.com/Le-Ptit-Collectionneur-St-Barthelemy.d553248621533158274.Vacation-Attraction)

### What to do in Leeward

![Coastal off-roading](https://mediaim.expedia.com/localexpert/2118561/cd66fd25-ebf2-4877-bb34-b4e511beaa57.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### For cruise passengers: Guided ATV Tour of Dutch & French St. Maarten

$660

per traveler

[](https://expedia.com/things-to-do/for-cruise-passengers-guided-atv-tour-of-dutch-french-st-maarten.a2118561.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

$27

per adult

**100%** of travellers recommend

[](https://expedia.com/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

$159

per adult

**90%** of travellers recommend

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

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

Explore a world of travel with Expedia

## Other vacations you might like

- Top cities in Leeward
- Best vacation destinations by month

- [St. Barthelemy Vacations ](https://expedia.com/St-Barthelemy.d6140949.Destination-Travel-Guides)

- [January Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-january)
- [February Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-february)
- [March Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-march)
- [April Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-april)
- [May Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-may)
- [June Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-june)
- [July Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-july)
- [August Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-august)
- [September Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-september)
- [October Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-october)
- [November Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-november)
- [December Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-december)

\* 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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