Philipsburg Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $2,455, price is now CA $1,327 per person
CA $1,327
per person
Jul 4 - Jul 8
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,682 reviews)
Stayed at the Simpson Bay Resort for our first trip to St. Maarten. It was a great stay! Easy access to popular restaurants and nightlife. Great beach views and access as well. The staff were very helpful and accommodating. Highly recommend, especially for a budget friendly option!

Reviewed on May 9, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $4,252, price is now CA $1,638 per person
CA $1,638
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,388 reviews)
We absolutely loved our stay at Simpson Bay Resort, Marina & Spa! The location was perfect, the views were beautiful, and the staff made us feel so welcome from the moment we arrived. We enjoyed relaxing by the beach and pool, and everything we needed was close by. The atmosphere was fun, peaceful, and exactly what we needed for a vacation. We’re already talking about coming back again. Highly recommend for anyone visiting St. Martin!

Reviewed on May 7, 2026

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was CA $2,798, price is now CA $1,799 per person
CA $1,799
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.4/10 Exceptional! (695 reviews)
We have awesome time

Reviewed on May 4, 2026

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $2,453, price is now CA $1,605 per person
CA $1,605
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,005 reviews)
Yes, everything was there. The continental breakfast was good.

Reviewed on May 7, 2026

Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was CA $2,827, price is now CA $1,885 per person
CA $1,885
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.6/10 Exceptional! (51 reviews)
I had a wonderful stay at Panorama Residences in St. Maarten! The property itself is absolutely beautiful, with stunning views that truly elevate the entire experience. The space was clean, comfortable, and felt like the perfect blend of relaxation and luxury—exactly what I was looking for during my trip. A special thank you to Nickey, the host, who was incredibly responsive, kind, and helpful throughout my stay. Communication was smooth from start to finish, and any questions or needs I had were handled quickly and professionally, which made everything stress-free. The location was also a huge plus—conveniently situated on a private hill, however, with still access to nearby beaches, restaurants, and activities while still offering a peaceful and private atmosphere. Overall, I highly recommend Panorama Residences to anyone visiting St. Maarten. I would absolutely stay here again!

Reviewed on May 5, 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?

 

Choose your dates

Philipsburg Hotel Deals

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Little Bay Road Philipsburg
Fully refundableReserve now, pay when you stay
The price is CA $245 per night from Jun 6 to Jun 7
CA $245
CA $318 total
Jun 6 - Jun 7
includes taxes & fees
8.2/10 Very Good! (1,016 reviews)
I really enjoyed my stay at the hotel. The property was clean and well maintained, and my room had a beautiful view overlooking the harbor. The room itself was spacious, and I especially loved the large porch where I could relax and enjoy the scenery. Overall, it was a comfortable and pleasant experience, ...

Reviewed on May 6, 2026

Divi Little Bay Beach Resort
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 $366 per night from Jun 3 to Jun 4
CA $366
CA $468 total
Jun 3 - Jun 4
includes taxes & fees
8.2/10 Very Good! (401 reviews)
I loved the privacy, beach, mostly room was clean, loved the balcony beach view, food was good. Phenomenal experience @ The spa Indulgence by the sea -massager was phenomenal- Avenicia Salomon -I scheduled 2x with her -she was possibly the best staff member I met along with Mimi from the breakfast@ ...

Reviewed on May 8, 2026

Oceans at Divi Little Bay
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 $345 per night from Jun 6 to Jun 7
CA $345
CA $414 total
Jun 6 - Jun 7
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
Beautiful beach view!

Reviewed on May 7, 2026

Holland House Beach Hotel
See all 3,597 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Philipsburg

Great Bay Beach

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

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

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

Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

CA $90
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

CA $104
per adult
80% of travellers recommend
High-Speed Ferry to St. Barths
Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

CA $117
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
See all activities in Philipsburg

Explore a world of travel with Expedia

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