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.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
CA $1,312
per person
Nov 8 - Nov 14
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,987 reviews)
the Front Desk staff upon arrival at check in was very gd...Monique was Exceptional n very friendly n helpful also so professional

Reviewed on Sep 23, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
CA $1,651
per person
Nov 9 - Nov 16
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,525 reviews)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond
Save 100% on your flight
CA $1,332
per person
Nov 9 - Nov 16
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
The staff is very friendly and accommodating. Beautiful views. The only thing I would ask is that water be restocked daily because it is easy to get dehydrated even if you buy your own water.

Reviewed on Sep 14, 2026

The Morgan Resort Spa Village

The Morgan Resort Spa Village

Save 100% on your flight
CA $2,013
per person
Nov 25 - Dec 1
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (2,390 reviews)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

Point Blanche
Save 100% on your flight
CA $1,625
per person
Nov 25 - Dec 1
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.6/10 Exceptional! (93 reviews)

Where to stay in Philipsburg

Find the best Philipsburg areas and neighborhoods for the activities you enjoy most. Learn more about Philipsburg
A coastal cityscape with a marina, residential buildings, and a mountainous backdrop.

Indigo Bay

While Indigo Bay isn't home to many top sights, Little Bay Beach and Indigo Beach are some notable places to visit nearby.

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A coastal town with buildings, a clear blue sea, and mountains in the background.

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 Front Street District.

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A large cruise ship docked at a pier with a mountainous coastline and sailboats in the background.

Point Blanche

1 out of top 10 points of interest in this area

While visiting Point Blanche, you might make a stop by sights like Port of St. Maarten and Harbour Point Village.

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A coastal town with a marina, mountains, and a bay.

Belair

While Belair isn't home to many top sights, Little Bay Beach and Great Bay Beach are some notable places to visit nearby.

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Default Image

Vineyard

If you're looking for some top things to see and do in Vineyard and surrounding area, you can visit Port of St. Maarten and Front Street District.

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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

Little Bay Road Philipsburg
Fully refundableReserve now, pay when you stay
CA $219
CA $286 total
Oct 3 - Oct 4
includes taxes & fees
8.2/10 Very good! (1,008 reviews)
"Good"

Reviewed on Sep 23, 2026

Divi Little Bay Beach Resort
Oceans at Divi Little Bay

Oceans at Divi Little Bay

Little Bay Road Philipsburg St. Maarten
Fully refundableReserve now, pay when you stay
CA $293
CA $378 total
Oct 1 - Oct 2
includes taxes & fees
Oceans at Divi Little Bay
Holland House Beach Hotel

Holland House Beach Hotel

Front Street 45 Philipsburg
Fully refundableReserve now, pay when you stay
CA $333
CA $415 total
Oct 23 - Oct 24
includes taxes & fees
Holland House Beach Hotel
See all 3,593 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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Stay near popular Philipsburg attractions

A turquoise beach with a wooden pier, a mountain in the background, and cruise ships docked in the water.

Great Bay Beach

9.0/10 (587 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.
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A pier with a red roof, flags, and a sign for 'S&Martin'.

Philipsburg Boardwalk

8.8/10 (97 reviews)
Philipsburg Boardwalk is just one of the places to see in Philipsburg, so why not enjoy the other things to explore during your travels? Stroll along the area's beaches or simply enjoy its restaurants.
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A coastal fortification with rusted cannons, a clear blue sea, and green hills in the background.

Fort Amsterdam

8.8/10 (245 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.
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A vintage yellow car parked on a cobblestone street lined with colorful buildings, including a Belgian Chocolate Box shop.
Photo by daniel jersey

Front Street District

You can search for that perfect souvenir at Front Street District during your trip to Philipsburg.
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Port of St. Maarten

Explore the waterfront in Philipsburg with a trip to Port of St. Maarten.
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Little Bay Beach

9.4/10 (366 reviews)
If a restful vacation is part of your travel plans, Little Bay Beach might be the perfect place to seek out during your trip to Philipsburg. Amble around this romantic area's seaside and enjoy its top-notch restaurants.
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Rainforest Adventures St. Maarten

You can take time to visit Rainforest Adventures St. Maarten during your travels to Philipsburg. Amble around this romantic area's beautiful beaches and enjoy its top-notch restaurants.
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Indigo Beach

8.0/10 (23 reviews)
Why not spend a lazy afternoon at Indigo Beach during your trip to Cole Bay?
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What to do in Philipsburg

Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

CA $91
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

CA $107
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
Mambo Catamaran Cruise to Rendezvous Bay Anguilla with Lunch

Mambo Catamaran Cruise to Rendezvous Bay Anguilla with Lunch

CA $189
per adult
86% of travellers recommend
Mambo Catamaran Cruise to Rendezvous Bay Anguilla with Lunch
See all activities in Philipsburg

Frequently asked questions

How much does a Philipsburg vacation package cost?
You can pick up a vacation package to this destination from CA $1,312 on Expedia. But how much your vacation to Philipsburg costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Philipsburg?
September, October and November are great times to look for cheap Philipsburg vacation packages. Opting to travel in less busy months means you can typically find reduced prices on hotels and flights.
How many days is enough for Philipsburg?
We'd suggest booking a Philipsburg vacation for a minimum of 4 days. This will give you enough time to visit top attractions such as Great Bay Beach and Grand Case Beach, and also check out neighbourhoods like Pelican Key and Upper Prince's Quarter. You could even fit in a day trip beyond Philipsburg.
Is it worth booking a vacation package to Philipsburg?
From leading attractions such as Great Bay Beach and Little Bay Beach to its excellent shopping, a Philipsburg vacation is sure to exceed your expectations. With so much to do and see, find out for yourself why Philipsburg is such a good vacation destination.
How to find the best Philipsburg package deals?
Use Expedia's filters to find some of the best Philipsburg package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Philipsburg package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Philipsburg vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and accommodations separately. Better still, you can personalize your Philipsburg getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Philipsburg?
If you're considering a spontaneous Philipsburg getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Philipsburg?
  1. Pick the perfect time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to Philipsburg.
  2. Plan your budget wisely: As well as the price of your hotel, you should factor in other expenses. These include food, transportation and flights. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Philipsburg.
  3. Work out your trip length: Think about how long you'd like to spend discovering Philipsburg. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Philipsburg vacation package.

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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.