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.
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Price was CA $1,834, price is now CA $1,162 per person
CA $1,162
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (960 reviews)
Its a beautiful property and the customer service experience is wonderful
Reviewed on Aug. 30, 2025
The Villas at Simpson Bay Resort
Price was CA $2,857, price is now CA $1,403 per person
CA $1,403
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,227 reviews)
No welcome drinks when we arrived. Limited excursions on certain days.
Reviewed on Sep. 2, 2025
Simpson Bay Resort, Marina & Spa
Pelican Key
Price was CA $2,476, price is now CA $1,279 per person
CA $1,279
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,291 reviews)
The property is beautiful, service reps were great. Food on the resort was delicious, excursions provided were very nice. It was affordable, but you do get what you pay for. I chose the least expensive room, and it was very nice, but the furthest away from everything, except its own pool, so lots of walking in the heat. The toilet and sink leaked. I called twice and no one came and it was never fixed. I ended up putting towels on the floor behind the toilet and next to the sink to absorb the water. We were leaving 2 1/2 days later, so I didn’t pursue it. Hopefully it’s fixed for the next customer. If I ever go back to St Martin, I would stay again in a different section of the resort.
Reviewed on Sep. 2, 2025
Holland House Beach Hotel
Downtown Philipsburg
Price was CA $3,040, price is now CA $1,757 per person
CA $1,757
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,003 reviews)
Wonderful stay. Only issue is the WiFi for the TV wasn’t stable but all else was amazing!
Reviewed on Aug. 27, 2025
Hilton Vacation Club Royal Palm St. Maarten
Price was CA $1,815, price is now CA $1,170 per person
CA $1,170
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,084 reviews)
Bar staff was the best from Morgan and her team.
Reviewed on Sep. 2, 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
Maho
4.5/5(2 area reviews)
While visiting Maho, you might make a stop by sights like Mullet Bay Beach and Mullet Bay.
Lesser Antilles Hotel Deals
Sonesta Maho Beach All Inclusive Resort Casino & Spa
1 Rhine Road, Maho Bay, Lowlands
The price is CA $287 per night from Sep 10 to Sep 11
CA $287
CA $347 total
Sep 10 - Sep 11
includes taxes & fees
Margaritaville Vacation Club - St. Thomas
6080 Estate Smith Bay, St. Thomas
The price is CA $346 per night from Sep 4 to Sep 5
CA $346
CA $389 total
Sep 4 - Sep 5
includes taxes & fees
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from Oct 1 to Oct 2
CA $114
CA $137 total
Oct 1 - Oct 2
includes taxes & fees
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.
Discover the most popular places to visit in Lesser Antilles
Sapphire Beach
Enjoy sunbathing, swimming and fun-filled watersports at this peaceful arched bay.
Magens Bay Beach
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.
Orient Bay Beach
Nothing says vacation like spending a lazy day at Orient Bay Beach, a popular beach in Orient Bay. Check out the top-notch restaurants or lively bars in this walkable area.
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Packages
General
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.