Title: Leeward Vacations & Trips 2026 from CA $4,293 | 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/1000000/10000/7000/6956/00bf2ae6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Tropical Hotel St Barth CA $4,293 per person Apr 24 - Apr 30 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) 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 ![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 CA $4,632 per person Jun 14 - Jun 19 found 7 hours ago Roundtrip flight included Montreal (YUL) 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 ![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 CA $6,156 per person Apr 24 - Apr 30 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Gustavia (SBH) 9.4/10 Exceptional! (68 reviews) 365 degrees of beauty the eye wanders off to more and more beauty! The staff is excellent, kind and so so lovely! The concierge took care of our every need! We’re definitely going to stay again! Reviewed on Mar 16, 2026 ![Christopher Hotel](https://images.trvl-media.com/lodging/1000000/10000/9500/9481/96a64866_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Christopher Hotel CA $5,673 per person May 18 - May 25 found 22 hours ago Roundtrip flight included Montreal (YMQ) to Gustavia (SBH) 9.6/10 Exceptional! (232 reviews) The entire staff was absolutely wonderful along with the view from the pool and room. The overall property needs to be updated and refreshed. Pool area, restaurants or lack of and room were tired. It does not look like the photos.The rug in the bedroom was so dirty with stains, we wore our shoes in the room. Also, it’s a far drive from everything and requires cabs back and forth. We stayed at Eden Rock last trip which was sold out and advised from friends for Christopher. If you are going to spend the money going to St Barths choose another resort for the total experience. Reviewed on Feb 26, 2026 ## Leeward Hotel Deals ![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 CA $1,852 CA $2,023 total Apr 9 - Apr 10 includes taxes & fees 9.4/10 Exceptional! (69 reviews) 365 degrees of beauty the eye wanders off to more and more beauty! The staff is excellent, kind and so so lovely! The concierge took care of our every need! We’re definitely going to stay again! Reviewed on Mar 16, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F04%2F2026&endDate=10%2F04%2F2026&selected=1182278&PinnedHotelID=1182278&HadPinnedHotel=true®ionId=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! (59 reviews) Excellent stay. Reviewed on Mar 22, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=08%2F04%2F2026&endDate=09%2F04%2F2026&selected=88474775&PinnedHotelID=88474775&HadPinnedHotel=true®ionId=553248635975177495) [](https://expedia.ca/Hotel-Search?startDate=08%2F04%2F2026&endDate=09%2F04%2F2026&selected=88474775&PinnedHotelID=88474775&HadPinnedHotel=true®ionId=553248635975177495) ![Pearl Beach Hotel](https://images.trvl-media.com/lodging/1000000/60000/54000/53985/ae1c759b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pearl Beach Hotel Plage De St. Jean BP1058 St. Barthelemy French West Indies CA $1,303 CA $1,368 total Mar 26 - Mar 27 includes taxes & fees 9.4/10 Exceptional! (191 reviews) Too close to Airport Reviewed on Jan 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F03%2F2026&endDate=27%2F03%2F2026&selected=53985&PinnedHotelID=53985&HadPinnedHotel=true®ionId=553248635975177495) [See all 1,460 properties in Leeward](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F03%2F2026&endDate=27%2F03%2F2026®ionId=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 ![St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island](https://mediaim.expedia.com/localexpert/686653/f4f02859-9575-4662-828a-ff234bbed1bf.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 $77 per adult **94%** 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 $37 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/amazing-plane-spotting-at-maho-beach.a1705818.activity-details) ![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 CA $903 per traveller **100%** of travellers recommend [](https://expedia.ca/things-to-do/for-cruise-passengers-guided-atv-tour-of-dutch-french-st-maarten.a2118561.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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app