Philipsburg Vacation Packages

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Your Philipsburg Vacation

Reserve a Philipsburg vacation package that has everything you need and no unnecessary extras. Great for shopping, coastal beaches and nature, consider basing yourself in the neighborhood of Upper Princes Quarter. If taking in sights is on the to-do list during your trip to Philipsburg, look around well-known attractions like Maho Beach, Pinel Island and Marigot Market. Browse Expedia's wide range of travel options and book your ideal vacation to Philipsburg today.

Top Philipsburg Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $2,659, price is now CA $1,466 per person
CA $1,466
per person
May 23 - May 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,007 reviews)
Staff was super friendly and helpful. The room was clean. The view from the balcony was amazing. If you stay I’d suggest renting a car as it’s far from the airport and shops too far to walk. Nearby markets were great and inexpensive. I’ll definitely go back and stay here one day.

Reviewed on Mar 19, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $4,278, price is now CA $1,782 per person
CA $1,782
per person
May 23 - May 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,629 reviews)
Great stay , ocean view room . Clean , very friendly and responsive staff!

Reviewed on Mar 19, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $4,455, price is now CA $1,880 per person
CA $1,880
per person
May 23 - May 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,387 reviews)
Resort was clean and transportation was readily accessible

Reviewed on Mar 17, 2026

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was CA $2,598, price is now CA $1,586 per person
CA $1,586
per person
May 23 - May 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.4/10 Exceptional! (668 reviews)
The hotel location is excellent to walk everywhere - beach, restaurants, shops. The staff is friendly, professional and knowledgeable, especially Elena. The room was spacious, clean and had everything you need for a relaxing beach vacation. The breakfast is improved from last year and has more options to choose from. The restaurant staff could improve in greeting clients and restaurant cleanness.

Reviewed on Mar 18, 2026

Where to stay in Philipsburg

Find the best Philipsburg areas and neighborhoods for the activities you enjoy most. Learn more about Philipsburg
Philipsburg St Maarten panoramic cityscape.

Downtown Philipsburg

3 out of top 10 points of interest in this area

While visiting Downtown Philipsburg, you might make a stop by sights like Great Bay Beach and Museum of Sint Maarten.

Find hotels in Downtown Philipsburg

Philipsburg Beach Vacation

There's nothing like a Philipsburg vacation to put a bounce in your step. The soothing rhythm of rolling waves and the smell of salty air are sure to rejuvenate your mind and body. To be near the city centre on your trip to Philipsburg, base yourself around Little Bay Beach (2 kilometres away). If you're going to stick around a while, consider booking one of our Philipsburg vacation deals. Not only can you save cash, you'll also have other beautiful beaches around you to explore, like Guana Bay Beach and Indigo Beach. We call that a win-win!

Things You Should Know About Philipsburg

  • Doze off to the calming sounds of the sea in one of our Philipsburg beach hotels. Nothing beats staying close to the ocean.
  • Philipsburg also has a decent selection of villas. The Paradise Inn and Oceans at Divi Little Bay are a hit with travellers and are worth taking a look at.
  • Around 1,400 people reside in Philipsburg. If you want suggestions about things to see and do, why not start a conversation with one or two of the locals? Our Philipsburg things to do page is also a handy source of information.
  • Once you've made some great savings by booking a Philipsburg vacation package, you can splurge on unforgettable travel experiences. Little Bay Beach, Sint Maarten Park and University of St. Martin are three attractions that should be on your itinerary.

Ready to book your vacation to Philipsburg?

 

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Philipsburg Hotel Deals

Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Little Bay Road Philipsburg St. Maarten
Fully refundableReserve now, pay when you stay
The price is CA $355 per night from Apr 6 to Apr 7
CA $355
CA $455 total
Apr 6 - Apr 7
includes taxes & fees
8.4/10 Very Good! (349 reviews)
Totally obstructed

Reviewed on Mar 15, 2026

Oceans at Divi Little Bay
The Paradise Inn

The Paradise Inn

3 out of 5
Senna road # 7 Philipsburg
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Mar 26 to Mar 27
CA $127
CA $135 total
Mar 26 - Mar 27
includes taxes & fees
8/10 Very Good! (385 reviews)
FANTASTIC PLACE

Reviewed on Mar 17, 2026

The Paradise Inn
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Front Street 45 Philipsburg
Fully refundableReserve now, pay when you stay
The price is CA $392 per night from Apr 20 to Apr 21
CA $392
CA $470 total
Apr 20 - Apr 21
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
For the price we paid, I expected much more from the restaurant. Food quality was average. Breakfast service was very slow.

Reviewed on Mar 19, 2026

Holland House Beach Hotel
See all 3,533 properties in Philipsburg
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 Philipsburg

Great Bay Beach showing general coastal views, a sandy beach and a coastal town

Great Bay Beach

4/5(20 reviews)

If a restful vacation is part of your travel plans, Great Bay Beach might be the perfect place to seek out during your trip to Philipsburg. Check out the shops and top-notch restaurants in this romantic area.

Great Bay Beach
Fort Amsterdam which includes château or palace, a ruin and military items

Fort Amsterdam

5/5(2 reviews)

The remains of the first Dutch military base in the Caribbean offer stunning views across the ocean and over the town of Philipsburg behind it.

Fort Amsterdam
Museum of Sint Maarten which includes art and interior views

Museum of Sint Maarten

Discover where the native population originally came from and learn about major events in the island’s colonial, social and natural past.

Museum of Sint Maarten

What to do in Philipsburg

Panoramic view of vibrant St. Martin

Edge Ferry Tickets to St. Barts

CA $137
per adult
84% of travellers recommend
Edge Ferry Tickets to St. Barts
Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

CA $89
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

CA $218
per adult
90% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
See all activities in Philipsburg

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.