A coastal town with a beach, rocky shoreline, and a mountain in the background.

Philipsburg Vacations from $934

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

The Latest Philipsburg Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Oct 10 - Oct 14

    The Villas at Simpson Bay Resort + Flight

    Pelican Key
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,490 reviews)
    "The grounds and the rooms were clean. All the employees were friendly and would say good morning when they saw you. The beaches are nice. A real soft sandy beach and one that is more rocky. Restaurants were good. Happy hour at the bars were great. I would definitely stay here again"
    Reviewed July 29, 2026
    Roundtrip New York (EWR) - Saint Martin (SXM)
    EWR - SXMNonstop SXM - EWR1 stop
    $2,081
    $934
    per traveler
    found 1 day ago
    The Villas at Simpson Bay Resort
  • Oct 2 - Oct 6

    Simpson Bay Resort, Marina & Spa + Flight

    Pelican Key
    4 nights
    4.0 star property
    9.0/10 - Wonderful (1,909 reviews)
    Roundtrip New York (EWR) - Saint Martin (SXM)
    EWR - SXM1 stop SXM - EWR1 stop
    Save 100% on your flight
    $1,754
    $941
    per traveler
    found 1 day ago
    Simpson Bay Resort, Marina & Spa
  • Sep 20 - Sep 25

    The Morgan Resort Spa Village + Flight

    Simpson Bay
    5 nights
    4.0 star property
    9.0/10 - Wonderful (2,320 reviews)
    "Rooms were not well cleaned daily"
    Reviewed July 29, 2026
    Roundtrip New York (EWR) - Saint Martin (SXM)
    EWR - SXM1 stop SXM - EWR1 stop
    Save 100% on your flight
    $2,038
    $1,164
    per traveler
    found 1 day ago
    The Morgan Resort Spa Village
  • Oct 20 - Oct 26

    La Playa Orient Bay + Flight

    Orient Bay
    6 nights
    4.0 star property
    9.4/10 - Exceptional (768 reviews)
    "Wonderful place! We have stayed twice!"
    Reviewed July 24, 2026
    Roundtrip New York (EWR) - Saint Martin (SXM)
    EWR - SXM1 stop SXM - EWRNonstop
    Save 100% on your flight
    $1,610
    $1,015
    per traveler
    found 1 day ago
    La Playa Orient Bay
  • Oct 2 - Oct 6

    Princess Heights Luxury Boutique Condo Hotel + Flight

    Oyster Pond
    4 nights
    3.5 star property
    9.2/10 - Wonderful (1,004 reviews)
    "L’hôtel est magnifique, avec une vue imprenable sur l’océan d’un côté et sur les montagnes de l’autre. Nous avions un appartement avec deux chambres, ce qui était parfait pour une famille de deux adultes et deux enfants. Chaque chambre avait sa propre salle de bain et il y avait deux balcons face à la mer. L’air climatisé était très efficace. L’hôtel était en parfait état et propre. Le gym était un bel atout pour les entraînements matinaux. La piscine était très agréable. Nous avons croisé des..."
    Reviewed July 23, 2026
    Roundtrip New York (EWR) - Saint Martin (SXM)
    EWR - SXM1 stop SXM - EWR1 stop
    $1,391
    $976
    per traveler
    found 1 day ago
    Princess Heights Luxury Boutique Condo Hotel

Where to stay in Philipsburg

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

Downtown Philipsburg

Downtown Philipsburg blends Caribbean charm with Dutch colonial architecture along its vibrant waterfront. Stroll the scenic boardwalk for breathtaking views of turquoise waters and cruise ships. Front Street buzzes with duty-free shops and local vendors selling jewelry, crafts, and souvenirs. The area comes alive with bars, restaurants, and casinos offering island entertainment and live music. Visit Sint Maarten Park or explore cultural spots like the Yoda Guy Movie Exhibit and Museum of Sint Maarten. Great Bay Beach provides perfect swimming conditions just steps from the shopping district.

Indigo Bay

This exclusive coastal haven on Sint Maarten's western shore offers a luxurious Caribbean escape with pristine beaches and upscale accommodations. White stucco buildings with red tile roofs dot the landscape, framed by carefully manicured tropical gardens. The turquoise waters invite you to unwind. The bay features scenic walking paths perfect for sunset strolls along the Caribbean Sea. Resort amenities include sophisticated beachfront lounges and water sports rentals. Travelers appreciate the peaceful atmosphere and premium dining options featuring fresh seafood and Caribbean-fusion cuisine.

Point Blanche

Point Blanche offers a glimpse of authentic Sint Maarten away from tourist crowds. This peaceful residential area features colorful Caribbean homes along coastal roads with breathtaking ocean views. Small, uncrowded beaches provide a secluded alternative to busier island spots. The neighborhood's quiet charm makes it perfect for travelers seeking a genuine local experience. Coastal walks reveal beautiful Caribbean vistas and natural tropical landscapes. While dining options are limited, nearby Philipsburg provides additional amenities just a short drive away.

Belair

Perched on hillsides above Little Bay, Belair offers luxury living with breathtaking Caribbean Sea panoramas. This upscale residential retreat features exclusive villas with infinity pools and modern Caribbean architecture. The neighborhood provides a peaceful alternative to Sint Maarten's busier tourist areas. The stunning ocean views and cooling trade winds create a perfect setting for relaxation. Though lacking shops or restaurants within its boundaries, Belair sits just minutes from Little Bay Beach and Great Bay Beach. Most visitors appreciate having rental cars to navigate the steep terrain and explore nearby Philipsburg.

Sucker Garden

Sucker Garden offers a peaceful retreat from Sint Maarten's tourist bustle. This residential neighborhood provides an authentic glimpse into island living with colorful Caribbean homes and friendly locals. Modest guesthouses and vacation rentals offer budget-friendly alternatives to expensive resorts. A short drive brings you to nearby attractions like Guana Bay Beach and Sint Maarten Park. The area features small family-run restaurants serving delicious local cuisine. Though quiet, the neighborhood's genuine character makes it perfect for travelers seeking value without sacrificing island charm.

Discover the most popular places to visit in Philipsburg

What to do in Philipsburg

Philipsburg Hotel Deals

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.

Frequently Asked Questions

How much does a Philipsburg vacation package cost?

You'll find cheap prices from $934 on Expedia for your Philipsburg break. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Philipsburg costs.

What are the cheapest months to go to Philipsburg?

You can typically find lower prices and better availability in June, October and December. Take a look at our cheap Philipsburg vacation packages and you could land some great off-season discounts.

How many days is enough for Philipsburg?

We recommend planning a Philipsburg vacation for around 4 days. This will give you enough time to tick off top attractions including Guana Bay Beach and Indigo Beach, as well as check out neighborhoods like Cay Bay Hill and Little Bay. You could even slot in a day trip (or two) outside of Philipsburg.

Is it worth booking a vacation package to Philipsburg?

Boasting a host of highlights starting with its amazing shopping, Philipsburg is a good vacation destination. Whether you'd like to check out attractions such as Little Bay Beach and Sint Maarten Park or take the road less traveled, you'll find plenty to see and do on your Philipsburg vacation.

How to find the best Philipsburg package deals?

Landing a cheap Philipsburg package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply some filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Philipsburg package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.

Is it cheaper to book a Philipsburg vacation as a package?

An Expedia vacation package could save you hundreds of dollars when compared to arranging stays and flights separately. Better still, you can customize your Philipsburg getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.

When to book a vacation package to Philipsburg?

Secure incredible bargains by reserving your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Philipsburg escape.

How to plan a trip to Philipsburg?

  1. Choose when to travel: Check your diary and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Philipsburg.
  2. Set your budget: Consider expenses such as flights, meals and transportation when working out how much to set aside for your trip to Philipsburg. Then, select a property that works with your budget, whether that's a wallet-friendly option or a more upscale getaway.
  3. Organize your Philipsburg escape with our trip planning tool: Look for and book stays and experiences all in one place. You can also collaborate with your group to plan an unforgettable trip to Philipsburg together.
  4. Decide how long to go for: Now that you're more familiar with Philipsburg, you can work out the ideal length of your vacation. Pull together a rough itinerary and give yourself enough time to get through everything on your must-do list.
  5. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose a Philipsburg vacation package that brings all your bookings together.
  6. Book any activities or day trips: Now to the fun part — organizing everything you want to see and do. Browse some of the exciting things to do in Philipsburg and reserve your tickets in advance to save time (and maybe some money too!).

Does Expedia offer Book Now, Pay Later Philipsburg vacation packages?

Secure your dream trip to Philipsburg with help from our Book Now, Pay Later vacations. No need to save like crazy or wait for your next payday — we've teamed up with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans allow you to spread the total cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to stick to your budget and snap up cheap deals while they last.

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