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.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was CA $1,968, price is now CA $1,340 per person
CA $1,340
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,010 reviews)
I genuinely want to personally Thank Jeremy and Nelson for their hospitality! They went above and beyond to make sure my wife and I were extremely comfortable. We felt completely safe and catered to with the care they showed us! I can’t forget what felt like our personal driver, Leticia! She’s absolutely amazing! I highly recommend requesting her if you need taxi services! You really made us feel at home! You guys are the best! Thank you so much! We can’t wait to come back and visit again! Much Love & Respect - Kela & Lany

Reviewed on Nov 7, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $3,327, price is now CA $1,790 per person
CA $1,790
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (2,129 reviews)
Overall great resort. Excellent staff and amenities.

Reviewed on Nov 7, 2026

Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was CA $4,344, price is now CA $2,869 per person
CA $2,869
per person
Dec 31 - Jan 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.6/10 Exceptional! (104 reviews)
Super clean, beautiful location. Friendly staff. Safe place. Will book again

Reviewed on Oct 24, 2026

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was CA $5,658, price is now CA $3,917 per person
CA $3,917
per person
Dec 20 - Dec 27
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.2/10 Very good! (1,001 reviews)
The location of property for snorkeling was great as you could easily swim in the bay and find a lot of really great snorkeling. The property was laid out to make it easy to get to things and shuttles were readily available. We initially gave our experience a rating of 2 due to issues with the toilet in the room and most importantly the attitude, laziness and work ethic of the staff members we encountered on day 1. After leaving an initial review of 2, our room was immediately corrected and the staff we encountered for the remainder of our vacation increased our experience rating from a 2 to a 4. The following employees were extremely pleasant and accommodating to us and treated us like family. Melissa (supv), Martin (supv), Caron, Rodger, Malik, Stephen, and Eline were all wonderful and made our trip great. The one thing that could have been better was the frequency of Live entertainment.. they only had entertainment for 2 nights during our stay and the band they had was phenomenal; bring them back more often. Divi Little Bay should have entertainment every night for a resort of that size. We will visit the resort again due to how our experience completely turned around after day 1. We met some great people and made some everlasting memories. See you next year!

Reviewed on Nov 6, 2026

Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was CA $5,601, price is now CA $3,926 per person
CA $3,926
per person
Dec 20 - Dec 27
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.4/10 Very good! (601 reviews)
Very friendly staff and experience! Room was very clean and well maintained.

Reviewed on Nov 5, 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

2 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

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 $325 per night from Dec 8 to Dec 9
CA $325
CA $419 total
Dec 8 - Dec 9
includes taxes & fees
8.4/10 Very good! (611 reviews)
"Very friendly staff and experience! Room was very clean and well maintained."

Reviewed on Nov 5, 2026

Oceans at Divi Little Bay
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 $296 per night from Nov 15 to Nov 16
CA $296
CA $381 total
Nov 15 - Nov 16
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
"The location of property for snorkeling was great as you could easily swim in the bay and find a lot of really great snorkeling. The property was laid out to make it easy to get to things and shuttles were readily available. We initially gave our experience a rating of 2 due to issues with the toilet ..."

Reviewed on Nov 6, 2026

Divi Little Bay Beach Resort
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Front Street 45 Philipsburg
The price is CA $414 per night from Dec 7 to Dec 8
CA $414
CA $497 total
Dec 7 - Dec 8
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Really great place to stay. Was passing through on my way to another island and stayed a couple if nights. Great staff, amenities and location. Breakfast was good value also. Two thumbs up. DH"

Reviewed on Nov 7, 2026

Holland House Beach Hotel
See all 3,617 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.
See properties

What to do in Philipsburg

Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

CA $92
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

CA $108
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
Sky Explorer & 360 Views

Sky Explorer & 360 Views

CA $83
per adult
78% of travellers recommend
Sky Explorer & 360 Views
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 $1,340 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.