Sint Maarten Mountain Vacations and Getaways

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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
$507
per person
Nov 17 - Nov 20
found 14 hours ago
Roundtrip non-stop flight included
New York (NYC) to Philipsburg (SXM)
9/10 Wonderful! (1,006 reviews)
We have returned to oyster Bay over and over again during the last 30 years. The staff are amazing and helpful the property is maintained very well , they have increased the choices of restaurants and the spa is also excellent !

Reviewed on Oct 17, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
Save 100% on your flight
$991
per person
Dec 18 - Dec 21
found 4 hours ago
Roundtrip flight included
Bridgetown (BGI) to Philipsburg (SXM)
9.2/10 Wonderful! (1,560 reviews)
Will be be back

Reviewed on Oct 17, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
Save 100% on your flight
$1,254
per person
Dec 18 - Dec 22
found 5 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Philipsburg (SXM)
9/10 Wonderful! (2,074 reviews)
Holland House Beach Hotel

Holland House Beach Hotel

Downtown Philipsburg
Save 100% on your flight
$1,371
per person
Dec 18 - Dec 21
found 4 hours ago
Roundtrip flight included
Bridgetown (BGI) to Philipsburg (SXM)
9.2/10 Wonderful! (1,004 reviews)
The meals at Ocean were phenomenal!

Reviewed on Oct 12, 2026

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

$951
per person
Dec 18 - Dec 21
found 4 hours ago
Roundtrip flight included
Bridgetown (BGI) to Philipsburg (SXM)
8.2/10 Very Good! (1,010 reviews)
We absolutely loved our beachfront room!!

Reviewed on Oct 14, 2026

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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

$1,757
per person
Dec 18 - Dec 21
found 4 hours ago
Roundtrip flight included
Bridgetown (BGI) to Philipsburg (SXM)
8.8/10 Excellent! (1,018 reviews)
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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
$946
per person
Nov 18 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Philipsburg (SXM)
9/10 Wonderful! (2,074 reviews)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
Save 100% on your flight
$991
per person
Dec 18 - Dec 21
found 4 hours ago
Roundtrip flight included
Bridgetown (BGI) to Philipsburg (SXM)
9.2/10 Wonderful! (1,560 reviews)
Will be be back

Reviewed on Oct 17, 2026

Holland House Beach Hotel

Holland House Beach Hotel

Downtown Philipsburg
Save 100% on your flight
$1,371
per person
Dec 18 - Dec 21
found 4 hours ago
Roundtrip flight included
Bridgetown (BGI) to Philipsburg (SXM)
9.2/10 Wonderful! (1,004 reviews)
The meals at Ocean were phenomenal!

Reviewed on Oct 12, 2026

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See all available trips from Columbus to Sint Maarten
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4 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
Save 100% on your flight
$1,254
per person
Dec 18 - Dec 22
found 5 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Philipsburg (SXM)
9/10 Wonderful! (2,074 reviews)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
Save 100% on your flight
$1,348
per person
Dec 18 - Dec 22
found 5 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Philipsburg (SXM)
9.2/10 Wonderful! (1,560 reviews)
The Atrium Beach Resort and Spa, an Ascend Collection Resort

The Atrium Beach Resort and Spa, an Ascend Collection Resort

Save 100% on your flight
$1,821
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Philipsburg (SXM)
8.8/10 Excellent! (1,003 reviews)
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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 $507. 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
Nov 3 - Nov 4
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 ...
9.2/10 Wonderful! (1,799 reviews)
"Great property, staff were even better! I will be back!"

Reviewed on Oct 17, 2026

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
$228 nightly
$237 total
Oct 20 - Oct 21
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! (1,583 reviews)
"Will be be back"

Reviewed on Oct 17, 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
$129 nightly
$135 total
Oct 19 - Oct 20
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 1,638 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
Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

$77
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
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.