Lesser Antilles Vacation Packages
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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 at Bolongo Bay and Magens Bay Beach — two popular attractions here. Another great city to add to your itinerary is Philipsburg. 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.
The Villas at Simpson Bay Resort
Pelican Key
CA $802
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,525 reviews)
Thank you guys for such an amazing stay. The staff were super professional and helpful. It’s such a big property and in walking distance to the strip. Everything was great! Thank you guys for exceptional service. The villas was dope. I plan to stay again. Thank you so much!
Reviewed on Sep 8, 2026
The Morgan Resort Spa Village
CA $1,187
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (2,390 reviews)
Very conveniently located to other restaurants and other hotels. Very quiet and relaxing.
I would definitely visiting again.
Reviewed on Sep 10, 2026
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
Maho
While visiting Maho, you might make a stop by sights like Mullet Bay Beach and Mullet Bay.
Maho Bay Quarter
If you're spending some time in Maho Bay Quarter, Maho Beach and Cinnamon Bay Beach are top sights worth seeing.
Esperanza
Stroll along the coastal boulevard and visit the collection of shops and restaurants on the main strip in the charming town.
Pelican Key
If you're spending some time in Pelican Key, Flamingo Beach and Hollywood Casino are top sights worth seeing.
Contant Farms
If you're spending some time in Contant Farms, Great Cruz Bay and Turner Bay are top sights worth seeing.
Ready to book your vacation to Lesser Antilles?
Lesser Antilles Hotel Deals
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
Fully refundableReserve now, pay when you stay
CA $219
CA $263 total
Sep 13 - Sep 14
includes taxes & fees
9/10 Wonderful! (2,009 reviews)
"Really satisfying"
Reviewed on Sep 10, 2026
The Morgan Resort Spa Village
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
CA $381
CA $499 total
Oct 11 - Oct 12
includes taxes & fees
9/10 Wonderful! (2,390 reviews)
"Very conveniently located to other restaurants and other hotels. Very quiet and relaxing. I would definitely visiting again."
Reviewed on Sep 10, 2026
The Westin St. Thomas Beach Resort & Spa
5 Estate Bakkeroe St. Thomas St. Thomas
CA $362
CA $521 total
Oct 2 - Oct 3
includes taxes & fees
8.4/10 Very good! (1,466 reviews)
"Excellent staff Amenities Great stay"
Reviewed on Sep 10, 2026
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.
Stay near popular Lesser Antilles attractions
Sapphire Beach
9.0/10 (1,479 reviews)
Enjoy sunbathing, swimming and fun-filled watersports at this peaceful arched bay.
Maho Beach
8.8/10 (2,865 reviews)
Nothing says vacation like spending a lazy day at Maho Beach, a popular beach in Maho Reef. Check out the top-notch restaurants or lively bars in this romantic area.
Trunk Bay
9.6/10 (1,107 reviews)
Backed by palms, this stretch of sparkling white sand is regularly ranked as one of the most beautiful beaches in the world.
Flamenco Beach
9.2/10 (225 reviews)
If a restful vacation is part of your travel plans, Flamenco Beach might be the perfect place to seek out during your trip to Culebra. Stroll along the seaside or seek out the snorkeling spots.
Magens Bay Beach
9.4/10 (1,559 reviews)
Appreciate the excellent views of hilly forests as you meander along a scenic trail on your way to this haven of white sand and inviting water.
Virgin Islands National Park
9.6/10 (899 reviews)
Hike on scenic trails, explore sugar plantation ruins and snorkel along an underwater trail in this pristine nature park, which covers much of St. John.
Photo by Waterlogged Travels
Bolongo Bay
8.2/10 (352 reviews)
Commune with nature and explore the great outdoors at Bolongo Bay during your travels in St. Thomas. Wander the beautiful beaches in this relaxing area.
Photo by Matt Anderson Photography
Jolly Beach
9.0/10 (789 reviews)
Why not spend a carefree afternoon at Jolly Beach during your travels in Jolly Harbour? While in this relaxing area, you can savor the top-notch restaurants.
Frequently asked questions
How much does a Lesser Antilles vacation package cost?
Explore the best of Lesser Antilles from as low as CA $802. We offer a great selection of hotels, flights and rental cars to suit every budget. Land even better deals when you add some sightseeing tours to your package.
How do I get a cheap travel package to Lesser Antilles?
Search for flights that suit your schedule, add a hotel to your booking and watch the savings stack up with a Lesser Antilles vacation package. It's as simple as that! From flights and hotels to tours and rental cars, Expedia makes traveling cheap and easy. And with more than 550 partner airlines and 1,000,000 hotel options around the globe to choose from, you won't be short of choice.
Where should I stay in Lesser Antilles?
St. Thomas is a terrific place to visit. This is where you'll find impressive sights including Magens Bay Beach and Coki Point Beach. Charlotte Amalie also draws in many travelers eager to check out some of the best attractions in Lesser Antilles. Some of the best are Blackbeards Castle and Fort Christian.
What are the top hotels in Lesser Antilles?
When it comes to hotels in St. Barthelemy, Christopher Hotel and Le Sereno are two excellent options. If you're visiting St. Thomas, Hilltop Villas At Bluebeard's Castle By Capital Vacations and Bunker Hill Hotel are waiting to welcome you.
How far in advance should I book my Lesser Antilles vacation?
Savvy travelers always book early. Airlines usually advertise flight tickets up to 12 months in advance, and this is a great opportunity to land some rock-bottom prices. Boss just told you to take your vacation time next week? No need to worry. Expedia are never short of fantastic deals to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Lesser Antilles travel package include?
Car rentals, flights and hotels — we connect you to the best deals. All you'll have to do is pick your ideal combination. Once you've made your booking, you can add on the exciting stuff like sightseeing activities. Our travel packages make it simple to put together an awesome Lesser Antilles vacation.
What should I know before booking a Lesser Antilles travel package?
Whether it's relaxation or adventure you're craving, a Lesser Antilles vacation package lets you plan your escape your way. Plus, you'll score great discounts just for combining your hotel with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Lesser Antilles Expedia vacation package?
Yes, you can. We have more than 550 airline partners worldwide, so pick the carrier that's a good fit for your travel preferences.
If I'm not able to travel, can I cancel my Lesser Antilles vacation package?
We understand — life doesn't always go according to plan. If you've locked in a Lesser Antilles vacation package and have to amend or cancel it, we can help. It's always worth browsing our Customer Service Portal first for information. But generally, if you've taken out your package within 24 hours, you may be able to cancel and rebook at no cost. If it's been longer than 24 hours, your hotel, airline or car rental company may impose a fee.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
