Sint Maarten Mountain Vacations 2026/2027

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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 Pond

$490

per person

Nov 18 - Nov 21

found 15 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9/10 Wonderful! (1,006 reviews)

Pros: Most of Staff were friendly, a lady at the desk when we came was not so much, she looked at us and carry on gossiping until another member of staff called her and hinted at her to tend to us. Hotel was clean. Room was cool due to working Air con. Cons: Room smelt damped as you walked in like its had water sitting around, moldy smell. It rained when we were there and the water was coming in under the front door into the room. The food was Okay, not as good as the local places around the island. The water pressure on the shower was really low so shower was not great.

Reviewed on Oct 19, 2026

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

$1,208

per person

Dec 19 - Dec 23

found 15 hours ago

Roundtrip non-stop flight included

New York (NYC) to Philipsburg (SXM)

9/10 Wonderful! (2,074 reviews)

It was great

Reviewed on Oct 19, 2026

The Villas at Simpson Bay Resort

Pelican Key

Save 100% on your flight

$1,021

per person

Dec 19 - Dec 22

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,560 reviews)

Will be be back

Reviewed on Oct 17, 2026

Divi Little Bay Beach Resort

$1,018

per person

Dec 19 - Dec 22

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to Philipsburg (SXM)

8.2/10 Very Good! (1,010 reviews)

The location was great, right on the beach and the water was clear and lovely to swim in. The air conditioning in our unit was unreliable and kept cutting out. Drinking water was not provided in the rooms and there were no fill (water) stations on the resort forcing guests to purchase water to stay hydrated. The room and food were adequate and overall the staff were friendly.

Reviewed on Oct 18, 2026

Sonesta Maho Beach All Inclusive Resort Casino & Spa

Save 100% on your flight

$1,692

per person

Dec 19 - Dec 23

found 15 hours ago

Roundtrip non-stop flight included

New York (NYC) to Philipsburg (SXM)

8/10 Very Good! (3,244 reviews)

Its was nice overall and most staff was friendly, but most of the dining areas were closed. The burger by the pool was supposed to open at 2pm and it never started serving until close to 4pm, the tavern was never open just the bar, the buffet was tiny and crowded, the swim up bar got very rowdy. For a family resort, that should be at the adult area. Maybe its because I was there during the renovations but very limited food. The Italian place was wonderful, we ate there twice. The kids club was nice,staff was wonderful with my daughter. Overall it wasnt bad, we chose it because it was close to the airport to see planes,but i dont think id stay again. Not worth paying for an all inclusive in my opinion

Reviewed on Oct 18, 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

Save 100% on your flight

$1,723

per person

Dec 19 - Dec 22

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) 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.

Oyster Bay Beach Resort

Oyster Pond

$490

per person

Nov 18 - Nov 21

found 15 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9/10 Wonderful! (1,006 reviews)

Reviewed on Oct 19, 2026

The Villas at Simpson Bay Resort

Pelican Key

Save 100% on your flight

$1,021

per person

Dec 19 - Dec 22

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,560 reviews)

Will be be back

Reviewed on Oct 17, 2026

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

$1,212

per person

Dec 26 - Dec 29

found 1 day ago

Roundtrip flight included

Port of Spain (POS) to Philipsburg (SXM)

9/10 Wonderful! (2,074 reviews)

It was great

Reviewed on Oct 19, 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.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

$757

per person

Nov 18 - Nov 22

found 15 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9.2/10 Wonderful! (1,001 reviews)

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

$1,208

per person

Dec 19 - Dec 23

found 15 hours ago

Roundtrip non-stop flight included

New York (NYC) to Philipsburg (SXM)

9/10 Wonderful! (2,074 reviews)

It was great

Reviewed on Oct 19, 2026

The Villas at Simpson Bay Resort

Pelican Key

Save 100% on your flight

$845

per person

Nov 18 - Nov 22

found 15 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9.2/10 Wonderful! (1,560 reviews)

Will be be back

Reviewed on Oct 17, 2026

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See all available trips from Columbus to Sint Maarten

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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 $490. 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

Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay

27 min walk from Maho Beach

$135 nightly

$142 total

Oct 26 - Oct 27

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! (1,800 reviews)

"Naomi was by far the best staff. She was very sweet & on top of everything. Room was nice. Able to section off from livingroom. Outdoor pool and grill area was nice. Balcony’s are nice. Smoking should be allowed outdoor on balcony."

Reviewed on Oct 19, 2026

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

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond Road No 156 Oyster Pond

12 min drive from Maho Beach

$129 nightly

$135 total

Oct 20 - Oct 21

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 ...

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.