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.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.6/10 Excellent! (891 reviews)
Over all will stay again

Reviewed on Jul. 15, 2025

Cupecoy Beach Club

Cupecoy Beach Club

3 out of 5
Maho
per person
Aug 26 - Aug 30
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (2 reviews)
Great location, spacious accomodations

Reviewed on May 24, 2025

Artimino by Island Properties Online

Artimino by Island Properties Online

3.5 out of 5
Maho
per person
Aug 24 - Aug 30
found 12 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
No reviews
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,192 reviews)
I like the property very much, our stay was very enjoyable. Our room was very comfortable,The staff was very helpful and friendly.

Reviewed on Jul. 24, 2025

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (938 reviews)
This was a great stay and the staff was very friendly. Highly recommend

Reviewed on Jul. 22, 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
Esperanza

Esperanza

Stroll along the coastal boulevard and visit the collection of shops and restaurants on the main strip in the charming town.

Find hotels in Esperanza

Ready to book your vacation to Lesser Antilles?

 

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Lesser Antilles Hotel Deals

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $268 per night from Jul 28 to Jul 29
CA $268
CA $362 total
Jul 28 - Jul 29
includes taxes & fees
8.8/10 Excellent! (1,774 reviews)
"The Morgan Resort and Spa was amazing. I loved my room. I was in the Penthouse Oceanfront Suite. The room was large and the bathroom had all the necessary amenities, including a makeup area, a standalone tub, and a shower. I loved the lighting in the bathroom and the lighting options in the bedroom. ..."

Reviewed on Jul. 22, 2025

The Morgan Resort Spa Village
The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

4.5 out of 5
5 Estate Bakkeroe, Po Box 7100, St. Thomas, St. Thomas
The price is CA $445 per night from Aug 25 to Aug 26
CA $445
CA $614 total
Aug 25 - Aug 26
includes taxes & fees
8.2/10 Very Good! (1,018 reviews)
"It is a very well maintained building. Service is great, but it is pricey! We had a great time!"

Reviewed on Jul. 22, 2025

The Westin St. Thomas Beach Resort & Spa
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
6080 Estate Smith Bay, St. Thomas
The price is CA $367 per night from Jul 30 to Jul 31
CA $367
CA $413 total
Jul 30 - Jul 31
includes taxes & fees
8/10 Very Good! (2,136 reviews)
"Our family stayed here for 10 days and we loved it. The sargassum does cause a bit of a bad odor but we weren't at the hotel during the day so it really wasn't a problem for us. We love that you can walk fro the resort over to Coki Beach which is a fabulous beach with restrooms, food and drinks. ..."

Reviewed on Jul. 22, 2025

Margaritaville Vacation Club - St. Thomas
See all 14,995 properties in Lesser Antilles
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.
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Discover the most popular places to visit in Lesser Antilles

Sapphire Beach which includes a sandy beach and tropical scenes

Sapphire Beach

4.5/5(5 reviews)

Enjoy sunbathing, swimming and fun-filled watersports at this peaceful arched bay.

Sapphire Beach
Magens Bay featuring a sandy beach

Magens Bay Beach

5/5(8 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.

Magens Bay Beach
Orient Bay Beach

Orient Bay Beach

4/5(65 reviews)

Why not spend a carefree afternoon at Orient Bay Beach during your travels in Orient Bay? Check out the lively bars or top-notch restaurants in this walkable area.

Orient Bay Beach

Frequently asked questions

How much does a Lesser Antilles vacation package cost?
Explore the best of Lesser Antilles from as low as CA $975. 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.