Sint Maarten Mountain Vacations and Getaways

Book a Mountain Hotel + Flight or Car together to unlock savings

Top Mountain vacation packages in Sint Maarten

Price found within the past 48 hours. Click for updated prices.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

Oyster Pond
$608
per person
Dec 7 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Philipsburg (SXM)
9/10 Wonderful! (1,006 reviews)
the property is secluded, very clean and the staff so helpful and kind. Very beautiful people all around. The hotel room very clean, it was not what I was expecting as far as a hotel room, it was an apartment. Bathroom with double sink, so you have space for that significant other. A nice king size bed waking up to a view, a wrap around balcony from the bedroom to the living room. Kitchen and dinning room to to fill all your personal needs. A home away from home, you feel you belong here, you even have a dishwasher and laundry machine. What else do you need? The grounds have a beautiful infinity pool, laundry mat, gift shop, a market store on the property, spa and gym. Two great restaurants. The only down part was the beach with the frequent storms have been washing up some seaweed waste covering the beach but its just a phase mother nature. There is so many places to go and do. Or you can stay at the resort and be pampered. The staff really go out of their way to take care of their guests. I will miss my favorite Bartender Jeffery and his colorful tasty cocktails. Thank you.

Reviewed on Oct 5, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
Save 100% on your flight
$761
per person
Dec 7 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Philipsburg (SXM)
9.2/10 Wonderful! (1,560 reviews)
Best place to stay while visiting St. Maarten. Everything is literally right there. The room was clean and looks just like the photos.

Reviewed on Oct 7, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
$747
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) to Philipsburg (SXM)
9/10 Wonderful! (2,074 reviews)
Plenty of restaurants at the resort and within walking distance. The pools were great, the ocean beautiful. The two times we had to call the front desk, our issue was handled fairly quick and satisfactorily.

Reviewed on Oct 6, 2026

Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

Oyster Pond
$856
per person
Dec 7 - Dec 12
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (119 reviews)
The condo and property was clean and well decorated and maintained. We had an awesome stay and will return.

Reviewed on Jul 19, 2026

Holland House Beach Hotel

Holland House Beach Hotel

Downtown Philipsburg
$801
per person
Dec 7 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Philipsburg (SXM)
9.2/10 Wonderful! (1,004 reviews)
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5* Mountain vacations in Sint Maarten

Price found within the past 48 hours. Click for updated prices.
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

$1,472
per person
Dec 7 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Philipsburg (SXM)
8.8/10 Excellent! (1,018 reviews)
Ok

Reviewed on Oct 5, 2026

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3 Night Mountain vacations in Sint Maarten

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
$747
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) to Philipsburg (SXM)
9/10 Wonderful! (2,074 reviews)
Plenty of restaurants at the resort and within walking distance. The pools were great, the ocean beautiful. The two times we had to call the front desk, our issue was handled fairly quick and satisfactorily.

Reviewed on Oct 6, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
Save 100% on your flight
$761
per person
Dec 7 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Philipsburg (SXM)
9.2/10 Wonderful! (1,560 reviews)
Best place to stay while visiting St. Maarten. Everything is literally right there. The room was clean and looks just like the photos.

Reviewed on Oct 7, 2026

Holland House Beach Hotel

Holland House Beach Hotel

Downtown Philipsburg
$801
per person
Dec 7 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Philipsburg (SXM)
9.2/10 Wonderful! (1,004 reviews)
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4 Night Mountain vacations in Sint Maarten

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond
Save 100% on your flight
$647
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Philipsburg (SXM)
9.2/10 Wonderful! (1,001 reviews)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
Save 100% on your flight
$795
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Philipsburg (SXM)
9.2/10 Wonderful! (1,560 reviews)
Best place to stay while visiting St. Maarten. Everything is literally right there. The room was clean and looks just like the photos.

Reviewed on Oct 7, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
$1,119
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
9/10 Wonderful! (2,074 reviews)
Plenty of restaurants at the resort and within walking distance. The pools were great, the ocean beautiful. The two times we had to call the front desk, our issue was handled fairly quick and satisfactorily.

Reviewed on Oct 6, 2026

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Find amazing mountains vacations in Sint Maarten

How to plan for a mountain vacation in Sint Maarten?

The first step to planning your mountain vacation to Sint Maarten is to decide what dates you want to go. In the winter months, fresh snowfall means you could hit the slopes at ski resorts near Sint Maarten, while summer invites you to enjoy scenic hikes. It's a good idea to choose the type of accommodation you'd prefer, too. On Expedia, you'll encounter a vast array of options in Sint Maarten, from famous chain hotels to charming cabins. The vacation planning page has more tips for organizing your Sint Maarten mountain vacation.

What amenities should I look for when booking a mountain resort in Sint Maarten?

When booking accommodation for your mountain vacation to Sint Maarten, check to see if where you're staying has heating. Sint Maarten's mountain air means it can feel fresh at night. If you're craving a special stay, look to see if the hotel offers mountain view rooms, or has a pool or hot tub to unwind in the evenings. Expedia's handy search filters include all these amenities and more, making it a breeze to book the right place to stay on your Sint Maarten vacation package.

Why should I choose a package for my mountain vacation in Sint Maarten?

Choosing a package for your Sint Maarten vacation often works out cheaper thanks to the savings you get for bundling up your flights and hotel. You'll typically find it costs more when booking these separately. On Expedia, the green label even shows you how much you're saving. Packages also tend to be more flexible, meaning it's more likely you can cancel for free in case your 2026 plans change. You can usually secure your package by paying a small upfront deposit, whereas booking flights separately requires full payment.

What does a Sint Maarten package typically include?

Return flight tickets, your accommodation, and applicable taxes are typically included when you book a mountain vacation package to Sint Maarten from $608. Hotels may include breakfast and Wi-Fi, while the airfare may include checked luggage. Certain resorts may even include ski passes. As each Sint Maarten vacation package is different, be sure to double-check what's included before you confirm. If you want a hassle-free trip, consider booking Sint Maarten all-inclusive vacation packages as these include all meals.

How can I book my Sint Maarten on Expedia?

Comparing some of the best deals using the search wizard is one of the first steps to booking your Sint Maarten mountain vacation on Expedia. Take advantage of the search filters to narrow down hundreds of options at the click of a button. If you've got a strict budget, use the maximum price filter to set your limit. When you've pinned down your Sint Maarten package vacation, book it in just a few clicks. You'll also have the option to spread the cost with Expedia's payment plans.

Why book your Sint Maarten mountain vacation with Expedia?

With meaty exclusive deals you won't find anywhere else, you'll keep more cash in your pocket when booking your Sint Maarten vacation package on Expedia. No matter your preferences or tastes, you'll find the right place to stay thanks to the wide selection of accommodation. There are even last-minute deals, too. And if that's not enough, join One Key for free. Expedia's reward program lets you earn points on eligible trips and also gives you access to juicy member-only discounts.

Can I cancel my mountain vacation package booking?

Yes, as most of Expedia's mountain vacation packages to Sint Maarten are flexible, you can often cancel for free. Doing so is easy, too—log in to the “Trips” section and follow the steps. Don't forget to double-check the cancellation policy before booking, as not all Sint Maarten vacation packages are flexible. The good news is Expedia will display this to you before payment. Take advantage of the free cancellation search filter so you'll be able to narrow down your search to view only flexible Sint Maarten vacation packages.

What types of mountain accommodations are available in Sint Maarten?

5-star hotels, cozy mountain lodges, and quaint bed and breakfasts are some of the most popular types of mountain accommodations for your vacation to Sint Maarten. Don't forget to use the filters to home in the amenities you'd like to have, too. Maybe it's a spacious suite with a mountain view or a traditional lobby with a fireplace—you'll find it all with Expedia's easy-to-use search wizard and wide choice of accommodation.

Top Mountain Sint Maarten Hotels

Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
  • 27 min walk from Maho Beach
$135 nightly
$142 total
Oct 23 - Oct 24
Total with taxes and fees
Book a stay at this beach resort in Simpson Bay. Enjoy free parking, a beach locale, and breakfast (surcharge). Our guests praise the pool and the helpful staff ...
Hilton Vacation Club Flamingo Beach St. Maarten
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Billy Folly Road No. 37A Simpson Bay
  • 27 min walk from Maho Beach
$183 nightly
$192 total
Oct 8 - Oct 9
Total with taxes and fees
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our ...
9.2/10 Wonderful! (1,578 reviews)
"Best place to stay while visiting St. Maarten. Everything is literally right there. The room was clean and looks just like the photos."

Reviewed on Oct 7, 2026

The Villas at Simpson Bay Resort
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond Road No 156 Oyster Pond
  • 12 min drive from Maho Beach
$182 nightly
$192 total
Nov 7 - Nov 8
Total with taxes and fees
Book a stay at this family-friendly hotel in Oyster Pond. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Princess Heights Luxury Boutique Condo Hotel
See all 1,645 properties in Sint Maarten
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.

Things to do

High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

$81
per adult
78% of travellers recommend
High-Speed Ferry to St. Barths
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

$159
per adult
90% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
Exploring beautiful St.Martin

Adventure Island Tour

$65
per adult
Adventure Island Tour
See all activities in Sint Maarten

More vacations you might like

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