Title: Lesser Antilles Vacation Packages & Trips 2026 from CA $1,601 | Expedia.ca [Lesser Antilles Travel Guide](https://expedia.ca/Lesser-Antilles.dx3000655870)[Hotels in Lesser Antilles](https://expedia.ca/Lesser-Antilles-Hotels.d3000655870.Travel-Guide-Hotels)[Vacation Rentals in Lesser Antilles](https://expedia.ca/Lesser-Antilles-Vacation-Rentals.d3000655870.Travel-Guide-VacationRentals)[Flights to Lesser Antilles](https://expedia.ca/Cheap-Flights-To-Lesser-Antilles.d3000655870.Travel-Guide-Flights)[Lesser Antilles Car Rentals](https://expedia.ca/Car-Rentals-In-Lesser-Antilles.d3000655870.Car-Rental-Guide) ![](https://images.trvl-media.com/place/3000655870/4e44b64c-f868-42db-a6b5-d230f6850ee4.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Lesser Antilles Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## 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 ### Your Lesser Antilles Vacation See and do more with a vacation package to Lesser Antilles. Whether you're going for the views, history, culture, or something else, our package deals make travel planning easy. With so many things to explore on a trip to Lesser Antilles, it can be difficult to know where to start. Kick off your journey in [Charlotte Amalie](https://www.expedia.ca/Charlotte-Amalie.d3289.Destination-Travel-Guides) at Bolongo Bay and Magens Bay Beach — two popular attractions here. Another great city to add to your itinerary is [Philipsburg](https://www.expedia.ca/Philipsburg.d3331.Destination-Travel-Guides). Be sure not to miss Maho Beach and Great Bay Beach. Start packing your suitcase, because your Lesser Antilles vacation is just a few clicks away with Expedia. ## Top Lesser Antilles Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Princess Heights Luxury Boutique Condo Hotel](https://images.trvl-media.com/lodging/1000000/570000/561400/561365/3eb207bd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Princess Heights Luxury Boutique Condo Hotel Oyster Pond CA $1,601 per person Jan 23 - Jan 30 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Philipsburg (SXM) 9.2/10 Wonderful! (973 reviews) Staff were amazing, rooms and bathrooms were clean and pool was wonderful. We would highly recommend this location for your vacation. It is on the quiet side but with a car you can go anywhere from here.There are also good restaurants in the area and as Dawn beach can be a bit rough, you can drive to any of the beautiful beaches on the island. Great Bay, Mullet, Friar's, Happy and Anse Marcel are our favourites. Enjoy! Reviewed on Dec 10, 2025 ![The Villas at Simpson Bay Resort](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/7e74429d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Villas at Simpson Bay Resort CA $2,858 per person Jan 23 - Jan 30 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Philipsburg (SXM) 9.2/10 Wonderful! (1,309 reviews) From check in to check out, and everything in between, it was a perfect stay. The staff were all friendly and helpful. The accommodations clean, comfortable and supplied with everything we needed. The location is wonderful. We look forward to staying here again soon. Reviewed on Dec 9, 2025 ![Simpson Bay Resort, Marina & Spa](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Simpson Bay Resort, Marina & Spa Pelican Key CA $3,188 per person Jan 31 - Feb 7 found 1 day ago Roundtrip non-stop flight included Halifax (YHZ) to Philipsburg (SXM) 9/10 Wonderful! (1,463 reviews) Nice location however with there being no side walks it’s a bit rough when having to make your way up the hill to the resort to the B section of the resort. Possibly extend the shuttle hours. Reviewed on Dec 9, 2025 ![The Morgan Resort Spa Village](https://images.trvl-media.com/lodging/18000000/17530000/17525000/17524915/bf19cc27_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Morgan Resort Spa Village CA $2,008 per person Jan 23 - Jan 30 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Philipsburg (SXM) 9/10 Wonderful! (1,866 reviews) It was okay. Nothing special . Pretty far from the downtown area. Everything is expensive at the resort. A bottle of water at the pool is 8$. Reviewed on Dec 8, 2025 ![Oceans at Divi Little Bay](https://images.trvl-media.com/lodging/75000000/74270000/74267800/74267774/fee04e6c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Oceans at Divi Little Bay CA $2,749 per person Jan 23 - Jan 30 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Philipsburg (SXM) 8.4/10 Very Good! (266 reviews) This was our second stay and it didn’t disappoint. We were sad that Seabreeze restaurant and pool were shut as we liked that area but there was a new a la carte in the buffet . The food was good and the resort was clean . My only criticism would be the staff as the majority weren’t particularly friendly. Reviewed on Dec 8, 2025 ## Where to stay in Lesser Antilles Find the best Lesser Antilles areas and neighborhoods for the activities you enjoy most. [Learn more about Lesser Antilles](https://expedia.ca/Lesser-Antilles.dx3000655870) ![Esperanza](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/243000/243374-Vieques-Island.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Esperanza Stroll along the coastal boulevard and visit the collection of shops and restaurants on the main strip in the charming town. [Find hotel + flight trips in Esperanza](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Esperanza&DestID=6084481&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/523000/523252-mullet-beach.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Maho 4.5/5(2 area reviews) While visiting Maho, you might make a stop by sights like Mullet Bay Beach and Mullet Bay. [Find hotel + flight trips in Maho](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Maho&DestID=553248635976398598&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Cinnamon Bay showing forest scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/117000/117023-St-Thomas-And-St-John.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Maho Bay Quarter If you're spending some time in Maho Bay Quarter, Maho Beach and Cinnamon Bay Beach are top sights worth seeing. [Find hotel + flight trips in Maho Bay Quarter](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Maho%20Bay%20Quarter&DestID=553248635975749486&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/540000/540317-pelican-key.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Pelican Key If you're spending some time in Pelican Key, Flamingo Beach and Lay Bay Beach are top sights worth seeing. [Find hotel + flight trips in Pelican Key](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Pelican%20Key&DestID=553248635976196664&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Contant Farms If you're spending some time in Contant Farms, Great Cruz Bay and Turner Bay are top sights worth seeing. [Find hotel + flight trips in Contant Farms](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Contant%20Farms&DestID=553248635976399752&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Ready to book your vacation to Lesser Antilles? Choose your dates ## Lesser Antilles Hotel Deals ![The Morgan Resort Spa Village](https://images.trvl-media.com/lodging/18000000/17530000/17525000/17524915/bf19cc27_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Morgan Resort Spa Village 2 Beacon Hill Road Simpson Bay Fully refundableReserve now, pay when you stay CA $381 CA $488 total Dec 16 - Dec 17 includes taxes & fees 8.8/10 Excellent! (1,879 reviews) Gabriel, Shamila, and Ravi were very professional and respectable. They help me with almost all of my questions and they provided me with the proper guidance. They let me feel that I had family members at St. Maarten. Reviewed on Dec 8, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F12%2F2025&endDate=17%2F12%2F2025&selected=17524915&PinnedHotelID=17524915&HadPinnedHotel=true®ionId=3000655870) ![Margaritaville Vacation Club - St. Thomas](https://images.trvl-media.com/lodging/12000000/11800000/11796200/11796106/29cf8be8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Margaritaville Vacation Club - St. Thomas 6080 Estate Smith Bay St. Thomas CA $515 CA $579 total Dec 12 - Dec 13 includes taxes & fees 7.8/10 Good! (2,319 reviews) The best ever. Highly recommended. Reviewed on Dec 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=12%2F12%2F2025&endDate=13%2F12%2F2025&selected=11796106&PinnedHotelID=11796106&HadPinnedHotel=true®ionId=3000655870) ![Simpson Bay Resort, Marina & Spa](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Simpson Bay Resort, Marina & Spa Billy Folly Road 37 Simpson Bay CA $378 CA $454 total Dec 15 - Dec 16 includes taxes & fees 8.8/10 Excellent! (1,512 reviews) Great staff, easy check in, clean room with daily cleaning, full kitchen. Amenities at resort were great including several restaurants, grocery, several pools, beach area, pool towels provided. Easy walk or short drive to additional variety of other off-site restaurants and shopping. . Reviewed on Dec 9, 2025 [](https://expedia.ca/Hotel-Search?startDate=15%2F12%2F2025&endDate=16%2F12%2F2025&selected=1256868&PinnedHotelID=1256868&HadPinnedHotel=true®ionId=3000655870) [See all 14,833 properties in Lesser Antilles](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F12%2F2025&endDate=13%2F12%2F2025®ionId=3000655870) 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) ### Discover the most popular places to visit in Lesser Antilles ![Sapphire Beach which includes a sandy beach and tropical scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/117000/117319-Sapphire-Beach.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Sapphire Beach 4.5/5(5 reviews) Enjoy sunbathing, swimming and fun-filled watersports at this peaceful arched bay. [](https://expedia.ca/Sapphire-Beach-St-Thomas.d6068151.Vacation-Attraction) ![Orient Bay Beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/540000/540271-orient-bay.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Orient Bay Beach 4/5(65 reviews) Nothing says vacation like spending a lazy day at Orient Bay Beach, a popular beach in Orient Bay. Check out the lively bars or top-notch restaurants in this romantic area. [](https://expedia.ca/Orient-Bay-Beach-Orient-Bay.d6005110.Vacation-Attraction) ![Trunk Bay which includes island views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/117000/117236-Trunk-Bay.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Trunk Bay 5/5(5 reviews) Backed by palms, this stretch of sparkling white sand is regularly ranked as one of the most beautiful beaches in the world. [](https://expedia.ca/Trunk-Bay-St-John.d6068195.Vacation-Attraction) ## Frequently asked questions ### Can I cancel my flight booking to Lesser Antilles due to COVID-19? ### What's the best way to find cheap flights to Lesser Antilles that have flexible change policies? ### What are some of the general tips for travelers to Lesser Antilles during the COVID-19 outbreak? > - Investigate if any travel restrictions apply to your origin and destination before booking. Also check if there are any requirements you'll need to follow on arrival, such as health testing. > - Wear a face mask during airport screening. A TSA employee will require you to temporarily lower your mask to verify your identity. > - Instead of handing a TSA employee your boarding pass, position it straight on the reader yourself. Then, hold it up for inspection. > - You're allowed to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on bag. This will need to be removed for screening. > - Remove items from your pocket, such as your keys, phone and wallet, and place them in your carry-on instead of the bins. This will minimize handling during screening. > - Separate any food you're carrying for X-ray screening. Placing it in a clear plastic bag and into a bin reduces the need for a TSA officer to touch and inspect your belongings. ### Which airlines fly to Lesser Antilles? ### How can I find cheap tickets to Lesser Antilles? ### How much is a flight to Lesser Antilles? ### What are the most popular airports to fly into in Lesser Antilles? ### When is the cheapest time to fly to Lesser Antilles? ### How much is a plane ticket to Lesser Antilles? ### Which airlines with flights to Lesser Antilles employ COVID-19 cleanliness policies? > - JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights. > - Cape Air - this airline is known for providing passenger masks and cleaning with disinfectant. > - American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant. ## Explore a world of travel with Expedia \* 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