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.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

Oyster Pond
CA $1,145
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (999 reviews)
Know how much difference the Euro 💶 and the American dollar

Reviewed on Aug 11, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
CA $1,641
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
Excellent location, close to many restaurants including several on site that my family loved. We enjoyed the pool, pool bars, and the beach. Coffee shop on site, groceries, souvenirs etc. Parking was adequate. Close to airport. Felt very safe.

Reviewed on Aug 12, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
CA $1,214
per person
Sep 26 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
You could walk to so many restaurants. All were good and food great. Only complaint some nights we had to hot water for showers. Great view and supermarket on site. Best location to go see everything

Reviewed on Aug 11, 2026

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond
CA $1,413
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,003 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 Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

CA $3,068
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,003 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 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.

Find hotels in Downtown 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.

Find hotels in Indigo Bay
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.

Find hotels in Point Blanche
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.

Find hotels in Belair
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.

Find hotels in Vineyard

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 $226
CA $299 total
Sep 9 - Sep 10
includes taxes & fees
8.2/10 Very good! (1,029 reviews)
"Overall it was a nice place. Only thing is to make sure everything in your room is in working order."

Reviewed on Aug 11, 2026

Divi Little Bay Beach Resort
Seaview Beach Hotel

Seaview Beach Hotel

#85C Front Street Philipsburg
Fully refundableReserve now, pay when you stay
CA $114
CA $137 total
Aug 25 - Aug 26
includes taxes & fees
7.2/10 Good! (888 reviews)
"Excellent location with everything nearby."

Reviewed on Aug 9, 2026

Seaview Beach Hotel
Holland House Beach Hotel

Holland House Beach Hotel

Front Street 45 Philipsburg
Fully refundableReserve now, pay when you stay
CA $329
CA $397 total
Aug 22 - Aug 23
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Very nice hotel, centrally located. The staff were very nice. My only complaint, the bathroom was very nice looking, but not functional."

Reviewed on Aug 10, 2026

Holland House Beach Hotel
See all 3,668 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
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations

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.
See properties
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.
See properties
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.
See properties
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.
See properties

Port of St. Maarten

Explore the waterfront in Philipsburg with a trip to Port of St. Maarten.
See properties

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.
See properties

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.
See properties

Indigo Beach

8.0/10 (23 reviews)
Why not spend a lazy afternoon at Indigo Beach during your trip to Cole Bay?
See properties

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 $1,145 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.

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.