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 $1,065
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
Great location and great for families. Huge property though. Pool and beach area were great. Room was large with all the amenities. Small grocery store within walking distance. A lot of restaurants nearby.

Reviewed on Aug 9, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
CA $1,072
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
The property was well kept and a good value. There are many restaurants in the area and it is close to night clubs. I did not enjoy the breakfast buffet served at the hotel. However, overall the food was good.

Reviewed on Aug 8, 2026

Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

CA $3,024
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,003 reviews)
Everyone was so friendly and accommodating. My husband and I will definitely be returning!

Reviewed on Aug 8, 2026

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond
CA $1,127
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,004 reviews)
This property is nice.. it almost felt deserted as we didn’t see anyone at night. It was very clean, comfortable and we had everything needed. My only complaint was the room needed more light. I’d stay here again .

Reviewed on Aug 8, 2026

Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

CA $2,641
per person
Sep 26 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Philipsburg (SXM)
8/10 Very good! (3,112 reviews)
Resort is outdated. Staff is rude. Food was 10/10 amazing. The beach is beautiful! No night life at the resort.

Reviewed on Aug 8, 2026

Where to stay in Philipsburg

Find the best Philipsburg areas and neighborhoods for the activities you enjoy most. Learn more about Philipsburg
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 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 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 Museum of Sint Maarten.

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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?

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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 $226
CA $299 total
Sep 9 - Sep 10
includes taxes & fees
Divi Little Bay Beach Resort
Seaview Beach Hotel

Seaview Beach Hotel

#85C Front Street Philipsburg
Fully refundableReserve now, pay when you stay
CA $115
CA $142 total
Sep 9 - Sep 10
includes taxes & fees
Seaview Beach Hotel
Holland House Beach Hotel

Holland House Beach Hotel

Front Street 45 Philipsburg
Fully refundableReserve now, pay when you stay
CA $330
CA $396 total
Aug 12 - Aug 13
includes taxes & fees
Holland House Beach Hotel
See all 3,673 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 beach with turquoise water, white sand, and buildings in the background.

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 beach with a wooden signboard about marine turtle conservation, a white building, and a coastline.

Guana Bay Beach

9.0/10 (92 reviews)
The picturesque shores of this tranquil bay provide a great opportunity to escape the crowds and jump in the crystal clear water for surfing or swimming.
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A white building with green shutters and a green door labeled "COURTHOUSE".

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
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

CA $190
per adult
90% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

CA $120
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
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 $1,065 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.