Dutch Antilles Ski Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Off The Beaten Track
  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Flight and Ski hotel deals in Dutch Antilles

Price found within the past 48 hours. Click for updated prices.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
CA $1,620
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,525 reviews)
Clean and big rooms, beautiful beach

Reviewed on Sep 20, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
CA $1,636
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,987 reviews)
La Playa Orient Bay

La Playa Orient Bay

Save 100% on your flight
CA $1,670
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.4/10 Exceptional! (786 reviews)
We got a room upgrade upon arrival and it was beautiful! The property is spotless, easy access to the beach and all good restaurants. Plan to come back in the near future.

Reviewed on Sep 18, 2026

The Morgan Resort Spa Village

The Morgan Resort Spa Village

Save 100% on your flight
CA $2,460
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (2,390 reviews)
Holland House Beach Hotel

Holland House Beach Hotel

Downtown Philipsburg
Save 100% on your flight
CA $1,703
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Dutch Antilles
View all trips

5* Ski holidays in Dutch Antilles

Price found within the past 48 hours. Click for updated prices.
JW Marriott St. Maarten Beach Resort & Spa

JW Marriott St. Maarten Beach Resort & Spa

Oyster Pond
CA $2,052
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (392 reviews)
We had numerous issues with it being low season, and not being told of all the closures, problems, and changes was very frustrating. I asked Expedia for help to receive significant remuneration from the hotel, but Expedia’s emails and phone calls were ignored for the last week. I am very disappointed in a JW Marriott treating us like we were supposed to just accept yellow water in the tub, restaurants and spa closures, etc., as the manager said they make repairs in the off season and don’t close. Like an incredibly special occasion visit was considered secondary in importance to their own desires to improve it for other people. I am very disappointed and wish that the hotel staff responded to Expedia’s emails and phone calls to make us feel better about the whole experience. The staff were very kind at the pool and around the property. We were kindly offered a discount on our food bills as a result of early morning fire alarms, but no other apologies were made to make this right. I would appreciate your reaching out to me or the Expedia team to fix this. I waited to write this until I was told you never responded, and I wish you would resolve it now please.

Reviewed on Sep 18, 2026

Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

Save 100% on your flight
CA $6,704
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,005 reviews)
Despite other reviews I have seen, I was very impressed with the service we received. All the staff were great and personable. The rooms were cleaned daily and the view from the room was amazing. The food was delicious. Azul was our favorite. The sunset was spectacular. I definitely recommend the Ocean Point.

Reviewed on Sep 19, 2026

La Samanna, A Belmond Hotel, St Martin

La Samanna, A Belmond Hotel, St Martin

CA $4,207
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.4/10 Exceptional! (249 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Dutch Antilles
View all trips

3 Night Ski holidays in Dutch Antilles

Price found within the past 48 hours. Click for updated prices.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
Save 100% on your flight
CA $810
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,525 reviews)
Clean and big rooms, beautiful beach

Reviewed on Sep 20, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
CA $1,194
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Philipsburg (SXM)
9/10 Wonderful! (1,987 reviews)
La Playa Orient Bay

La Playa Orient Bay

Save 100% on your flight
CA $869
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9.4/10 Exceptional! (786 reviews)
We got a room upgrade upon arrival and it was beautiful! The property is spotless, easy access to the beach and all good restaurants. Plan to come back in the near future.

Reviewed on Sep 18, 2026

Don't see what you're looking for?
See all available trips from Columbus to Dutch Antilles
View all trips

4 Night Ski holidays in Dutch Antilles

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

Simpson Bay Resort, Marina & Spa

Pelican Key
CA $1,029
per person
Nov 23 - Nov 27
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
9/10 Wonderful! (1,987 reviews)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
Save 100% on your flight
CA $1,231
per person
Nov 11 - Nov 15
found 19 hours ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,525 reviews)
Clean and big rooms, beautiful beach

Reviewed on Sep 20, 2026

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond
Save 100% on your flight
CA $1,059
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
The staff is very friendly and accommodating. Beautiful views. The only thing I would ask is that water be restocked daily because it is easy to get dehydrated even if you buy your own water.

Reviewed on Sep 14, 2026

Don't see what you're looking for?
See all available trips from Columbus to Dutch Antilles
View all trips

Plan the ultimate ski vacation in Dutch Antilles

What are some benefits when booking ski vacations in Dutch Antilles?

If you're interested in skiing, there's nothing quite like a ski vacation. These trips are designed to allow you to enjoy being on the slopes and relax in tranquil and convenient accommodations at the end of the day. Amenities on ski trips can be pretty upscale, so it's easy to relax in a hot tub or at a spa in between your skiing excursions. Plus, they can put you right next to the slopes. You'll even find a variety of different vacation types available whether you're looking for family friendly, cheap, or even last minute ski vacations.

How can I book the best ski vacation in Dutch Antilles?

It is most important to implement the ski filter in your search when trying to find a ski vacation that will make you happy. Using the filter will automatically remove any entries that don't offer the skiing opportunities you want. After that, you'll need to think about what specifically you want from Dutch Antilles, and think about the time of year that's best to visit.

How can I find cheap ski vacations?

Cheap ski vacations are readily available in Dutch Antilles with some as cheap as CA $810. You can see the cheapest options by sorting your accommodation choices by price, which automatically puts the least-expensive results at the top of the list. You may also want to consider an accommodation with a kitchen, so you can cook instead of eating out.

Can I book ski packages?

Yes, ski packages are readily available throughout Dutch Antilles. All you have to do is put in your travel dates and see what's available. When you book a ski package, you may be able to enjoy discounts with savings of up to 59 when you book your accommodation and your flight together.

What should I consider when booking family ski vacations?

The key to a successful family ski vacation is ensuring that your family is kept happy and entertained. Consider what your family members are interested in and the kind of vacation they want. If they have little skiing experience, for example, you may want to opt for an accommodation that offers ski lessons or a kid's club. Various slope difficulties may be essential in providing opportunities for everyone at Dutch Antilles.

Can I book all-inclusive ski vacations in Dutch Antilles?

Yes, all-inclusive ski trips are available and may be precisely what you're looking for. All you have to do is include the filter for all-inclusive stays, and your search results will only show the accommodations that provide this handy feature that allows you to plan your entire trip to Dutch Antilles in advance.

What's the best time of year to plan a ski trip?

The apparent answer to when you should plan a ski trip is in winter, but other details are important too. If you book for Dutch Antilles's high season around January and February, you'll likely find increased prices. It's generally best to opt for the early or late season in December and April, as prices tend not to be quite as high.

How can I find the best deals on ski packages in Dutch Antilles?

When you're looking for cheap ski vacations, there are a few factors you can take advantage of to help get the best deals. Travelling during the off-season can be cheaper since there's more availability. However, the beginning and end of the season tend to be the most affordable for skiing.

Can I book a ski vacation that's fully refundable?

Being fully refundable is a feature you'll find on several accommodation packages in Dutch Antilles. You can even search for it explicitly using a filter for full refundability.

Why should I book a ski vacation package with Expedia?

When you book with Expedia, you'll find everything you need for cheap ski vacations, luxury ski vacations and everything in between in one central location. You may even be able to enjoy discounts for booking your accommodation and your flight together with savings of up to 59. With Expedia Rewards, you can earn points towards your next booking.

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.