Madeira Island Ski Vacations 2026

Top Ski vacation packages in Madeira Island

Price found within the past 48 hours. Click for updated prices.

Madeira Regency Cliff

$387

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

9.2/10 Wonderful! (311 reviews)

Lovely hotel excellent staff

Reviewed on Jul 28, 2026

Pestana CR7 Funchal

Save 100% on your flight

$410

per person

Dec 17 - Dec 20

found 1 day ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

8.8/10 Excellent! (289 reviews)

Awesome location, we enjoyed spending time at the pool with a great view on the city.

Reviewed on Sep 20, 2026

Pestana Carlton Madeira Ocean Resort Hotel

$1,422

per person

Oct 27 - Nov 1

found 17 hours ago

Roundtrip non-stop flight included

New York (NYC) to Funchal (FNC)

9/10 Wonderful! (1,001 reviews)

It is a beautiful hotel, we had a balcony with an ocean view. The breakfast is first class, the service was hospitable. And the location was perfect for us - only a 20 minute walk to the Funchal Marina, with an abundance of beautiful cafe's and shops. I would definitely recommend this hotel.

Reviewed on Sep 22, 2026

Pestana Promenade Ocean Resort Hotel

$1,279

per person

Oct 27 - Nov 1

found 17 hours ago

Roundtrip non-stop flight included

New York (NYC) to Funchal (FNC)

9.2/10 Wonderful! (691 reviews)

Good

Reviewed on May 15, 2026

Pestana Village Garden Hotel

Save 100% on your flight

$451

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

8.8/10 Excellent! (508 reviews)

Nice property. Probably great for kids. Prices reasonable. Walking distance in Funchal to downtown and the waterfront. Negative. The bed was hard as a rock.

Reviewed on Jun 21, 2026

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5* Ski vacations in Madeira Island

Price found within the past 48 hours. Click for updated prices.

Pestana Casino Park Ocean and SPA Hotel

$1,108

per person

Nov 26 - Dec 1

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Funchal (FNC)

8.6/10 Excellent! (1,001 reviews)

All good

Reviewed on Sep 19, 2026

Pestana Carlton Madeira Ocean Resort Hotel

$1,422

per person

Oct 27 - Nov 1

found 17 hours ago

Roundtrip non-stop flight included

New York (NYC) to Funchal (FNC)

9/10 Wonderful! (1,001 reviews)

Reviewed on Sep 22, 2026

Pestana Grand Premium Ocean Resort

Save 100% on your flight

$1,632

per person

Oct 25 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Funchal (FNC)

9/10 Wonderful! (592 reviews)

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3 Night Ski vacations in Madeira Island

Price found within the past 48 hours. Click for updated prices.

Pestana Casino Park Ocean and SPA Hotel

Save 100% on your flight

$407

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

8.6/10 Excellent! (1,001 reviews)

All good

Reviewed on Sep 19, 2026

Pestana Grand Premium Ocean Resort

Save 100% on your flight

$417

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

9/10 Wonderful! (592 reviews)

Pestana CR7 Funchal

Save 100% on your flight

$410

per person

Dec 17 - Dec 20

found 1 day ago

Roundtrip flight included

Lisbon (LIS) to Funchal (FNC)

8.8/10 Excellent! (289 reviews)

Awesome location, we enjoyed spending time at the pool with a great view on the city.

Reviewed on Sep 20, 2026

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4 Night Ski vacations in Madeira Island

Price found within the past 48 hours. Click for updated prices.

Pestana Ocean Bay Resort

$1,033

per person

Nov 6 - Nov 10

found 21 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Funchal (FNC)

8.4/10 Very Good! (260 reviews)

After moving to an air conditioned room and getting the premium drinks upgrade our stay definitely improved. The staff were amazing and went out of their way to help you with whatever you ask. Evenings entertainment showed some great talent, most singers were amazing. Daytime activities were fun but were limited to very few. System for the shuttle bus to town could be improved as it was a free for all and people had to eventually get back off. Breakfast and lunch options were good however dinner was a hit or miss and we ate out a few times as a result. I would recommend this hotel as its waterfront location is beautiful however only if you get the upgraded options.

Reviewed on Sep 20, 2026

Pestana Vila Lido Madeira Ocean Hotel

$1,125

per person

Nov 28 - Dec 1

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Funchal (FNC)

9.4/10 Exceptional! (295 reviews)

Casa Velha do Palheiro, Relais & Chateaux

$1,558

per person

Nov 6 - Nov 10

found 21 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Funchal (FNC)

9.6/10 Exceptional! (108 reviews)

If it’s your first time in Madeira I’d suggest staying somewhere in city center, it takes 15 mins to get to this hotel. Very nice property and amenities. The staff and service is weak , shortage of staff. The breakfast buffet for a 5 starvhotel and the price was so weak as weak.

Reviewed on Aug 9, 2026

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What are some things I should consider when booking a Madeira Island ski trip package?

Yes, you want pristine powder and perfect runs, but take a moment to consider how close you want to be to the slopes, what extras you want from your resort, and—of course—how much après ski you intend to indulge in.

How can I find cheap Madeira Island ski packages?

Right now, ski trips start at just $387. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Madeira Island?

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Madeira Island. Book lessons so you can gear up to take on the rest of the mountain with confidence. Après awaits for all after an eventful day in the snow.

How much does a ski trip to Madeira Island cost?

Sensational ski trips to Madeira Island start from $387. Use the budget filter to find powder at your perfect price. As always, prices and availability are subject to change. Additional terms may apply.

When’s the best time of year to plan a ski trip to Madeira Island?

The best time to hit the slopes in Madeira Island depends on what you’re looking for. If you’re all about powder-packed pistes and brilliant blue-sky skiing conditions, aim for the middle of the season. Alternatively, if you’re willing to take a chance on start or end of season snow, you’ll bag much cheaper prices —just make sure there’s a spa or après bar to shelter in on white-out days.

Can I book Madeira Island ski packages with airfare?

Save money on your snow time by booking your accommodation, airfare, and car rental in a brilliant bundle. It’s both convenient and cash-flow friendly.

Can I book a Madeira Island ski trip with free cancellation and/or flexible dates?

Flexibility is always a bonus when you’re flying down the slopes—and it makes for an easier booking process, too. Check the payment option filter to find trips with free cancellation as well as buy now, pay later options.

Why should I book a ski package in Madeira Island with Expedia?

Simple search and fantastic filters make it easy to find, build, and book your dream Madeira Island ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.