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
Price was CA $1,845, price is now CA $1,356 per person
CA $1,356
per person
Jan 9 - Jan 14
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,010 reviews)

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $3,246, price is now CA $1,665 per person
CA $1,665
per person
Jan 13 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,001 reviews)
My cousin and I had a great overnight stay @ your hotel. The staff was very helpful. Paul was great !!!

Reviewed on Oct 24, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Save 100% on your flight
Price was CA $4,230, price is now CA $2,344 per person
CA $2,344
per person
Jan 9 - Jan 14
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,584 reviews)

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
Price was CA $3,057, price is now CA $1,811 per person
CA $1,811
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (2,129 reviews)
Great location, close to the strip and the beach

Reviewed on Oct 26, 2026

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Price was CA $3,292, price is now CA $2,330 per person
CA $2,330
per person
Jan 13 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
The meals at Ocean were phenomenal!

Reviewed on Oct 12, 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
A sunset over a calm sea with several boats, a sandy beach, and a distant mountain range.

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

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37 Simpson Bay
The price is CA $254 per night from Oct 28 to Oct 29
CA $254
CA $305 total
Oct 28 - Oct 29
includes taxes & fees
9/10 Wonderful! (2,152 reviews)
"Great location, close to the strip and the beach"

Reviewed on Oct 26, 2026

Simpson Bay Resort, Marina & Spa
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 $600 per night from Oct 28 to Oct 29
CA $600
CA $735 total
Oct 28 - Oct 29
includes taxes & fees
9/10 Wonderful! (2,428 reviews)
"The staff was very accommodating , resort was clean, Salt restaurant was better than I expected. I would definitely stay here again."

Reviewed on Oct 26, 2026

The Morgan Resort Spa Village
Bluebeard's Castle Resort

Bluebeard's Castle Resort

4 out of 5
1331 Estate Taarneberg Charlotte Amalie Saint Thomas
The price is CA $248 per night from Nov 25 to Nov 26
CA $248
CA $307 total
Nov 25 - Nov 26
includes taxes & fees
Bluebeard's Castle Resort
See all 15,392 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Lesser Antilles attractions

A beach with clear turquoise water, a large tree, and a distant hill with buildings.

Sapphire Beach

9.0/10 (1,479 reviews)
Enjoy sunbathing, swimming and fun-filled watersports at this peaceful arched bay.
See properties

Frequently asked questions

How much does a Lesser Antilles vacation package cost?
Explore the best of Lesser Antilles from as low as CA $1,356. 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.