Title: Madeira Island Ski Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/602987/f8049d4a-b9e5-4742-9506-d35dbeaa1043.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Madeira Island Ski Vacations ## Book a Ski Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 ## Top Ski vacation packages in Madeira Island Price found within the past 48 hours. Click for updated prices. ![Pestana Churchill Bay](https://images.trvl-media.com/lodging/36000000/35780000/35774200/35774151/c4b77548_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pestana Churchill Bay $1,537 per person May 26 - Jun 1 found 22 hours ago Roundtrip non-stop flight included Boston (BOS) to Funchal (FNC) 9.6/10 Exceptional! (142 reviews) The Hotel and staff were really charming. Location excellent and enjoyed sitting outside with a drink watching the tourists having their picture taken with ‘Winston’ buzzy little town with good connections to Funchal. Will happily come back. Food was also very good Reviewed on Feb 21, 2026 ![Pestana Carlton Madeira Ocean Resort Hotel](https://images.trvl-media.com/lodging/1000000/20000/14400/14327/117e4530_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pestana Carlton Madeira Ocean Resort Hotel Save 100% on your flight $1,601 per person May 26 - Jun 1 found 22 hours ago Roundtrip non-stop flight included Boston (BOS) to Funchal (FNC) 8.8/10 Excellent! (1,001 reviews) Gym could have had a rowing machine Reviewed on Apr 2, 2026 ![Pestana Casino Park Ocean and SPA Hotel](https://images.trvl-media.com/lodging/1000000/20000/14400/14349/b10be447_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pestana Casino Park Ocean and SPA Hotel $1,540 per person May 26 - Jun 1 found 22 hours ago Roundtrip non-stop flight included Boston (BOS) to Funchal (FNC) 8.6/10 Excellent! (1,002 reviews) The mountain view and Ocean views were impressive. Excellent service, food, great waiters - the best and so neat the city centre. Beautiful hotel and staff. Clean and great facilities with infinity pool and spa. Reviewed on Mar 25, 2026 ![Pestana Fisherman Village](https://images.trvl-media.com/lodging/69000000/68610000/68601600/68601519/w2800h1862x0y3-92403779_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pestana Fisherman Village $1,573 per person May 26 - Jun 1 found 22 hours ago Roundtrip non-stop flight included Boston (BOS) to Funchal (FNC) 9/10 Wonderful! (50 reviews) Amazing staff, great rooms but a little dark, guys breakfast. Reviewed on Jan 16, 2026 ![Pestana Miramar Garden & Ocean Resort](https://images.trvl-media.com/lodging/1000000/870000/863900/863868/368e0364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pestana Miramar Garden & Ocean Resort $1,576 per person May 26 - Jun 1 found 22 hours ago Roundtrip non-stop flight included Boston (BOS) to Funchal (FNC) 8.8/10 Excellent! (123 reviews) We really enjoyed staying at this hotel - quiet peaceful setting in beautiful gardens. Would definitely return. Reviewed on Jul 13, 2024 Don't see what you're looking for? See all available trips from Columbus to Madeira Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-04/2026-05-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=FNC&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski vacations in Madeira Island Price found within the past 48 hours. Click for updated prices. ![Pestana Casino Park Ocean and SPA Hotel](https://images.trvl-media.com/lodging/1000000/20000/14400/14349/b10be447_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pestana Casino Park Ocean and SPA Hotel $1,540 per person May 26 - Jun 1 found 22 hours ago Roundtrip non-stop flight included Boston (BOS) to Funchal (FNC) 8.6/10 Excellent! (1,002 reviews) The mountain view and Ocean views were impressive. Excellent service, food, great waiters - the best and so neat the city centre. Beautiful hotel and staff. Clean and great facilities with infinity pool and spa. Reviewed on Mar 25, 2026 ![Pestana Carlton Madeira Ocean Resort Hotel](https://images.trvl-media.com/lodging/1000000/20000/14400/14327/117e4530_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pestana Carlton Madeira Ocean Resort Hotel Save 100% on your flight $1,601 per person May 26 - Jun 1 found 22 hours ago Roundtrip non-stop flight included Boston (BOS) to Funchal (FNC) 8.8/10 Excellent! (1,001 reviews) Gym could have had a rowing machine Reviewed on Apr 2, 2026 ![Pestana Vila Lido Madeira Ocean Hotel](https://images.trvl-media.com/lodging/1000000/870000/863000/862912/d71714de_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pestana Vila Lido Madeira Ocean Hotel $1,684 per person May 26 - Jun 1 found 22 hours ago Roundtrip non-stop flight included Boston (BOS) to Funchal (FNC) 9.4/10 Exceptional! (271 reviews) The staff was phenomenal! The rooms were comfortable and roomy. Everything was clean. We enjoyed our stay. Five minute walk to the beach! Reviewed on Mar 28, 2026 Don't see what you're looking for? See all available trips from Columbus to Madeira Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-04/2026-05-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=FNC&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski vacations in Madeira Island Price found within the past 48 hours. Click for updated prices. ![Pestana Carlton Madeira Ocean Resort Hotel](https://images.trvl-media.com/lodging/1000000/20000/14400/14327/117e4530_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pestana Carlton Madeira Ocean Resort Hotel $1,201 per person Jun 13 - Jun 15 found 1 day ago Roundtrip non-stop flight included New York (NYC) to Funchal (FNC) 8.8/10 Excellent! (1,001 reviews) Gym could have had a rowing machine Reviewed on Apr 2, 2026 ![Pestana Fisherman Village](https://images.trvl-media.com/lodging/69000000/68610000/68601600/68601519/w2800h1862x0y3-92403779_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pestana Fisherman Village $1,263 per person Jun 13 - Jun 15 found 1 day ago Roundtrip non-stop flight included New York (NYC) to Funchal (FNC) 9/10 Wonderful! (50 reviews) Amazing staff, great rooms but a little dark, guys breakfast. Reviewed on Jan 16, 2026 ![Pestana Casino Park Ocean and SPA Hotel](https://images.trvl-media.com/lodging/1000000/20000/14400/14349/b10be447_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pestana Casino Park Ocean and SPA Hotel $1,775 per person May 23 - May 25 found 23 hours ago Roundtrip non-stop flight included New York (NYC) to Funchal (FNC) 8.6/10 Excellent! (1,002 reviews) The mountain view and Ocean views were impressive. Excellent service, food, great waiters - the best and so neat the city centre. Beautiful hotel and staff. Clean and great facilities with infinity pool and spa. Reviewed on Mar 25, 2026 Don't see what you're looking for? See all available trips from Columbus to Madeira Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-04/2026-05-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=FNC&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski vacations in Madeira Island Price found within the past 48 hours. Click for updated prices. ![Pestana Carlton Madeira Ocean Resort Hotel](https://images.trvl-media.com/lodging/1000000/20000/14400/14327/117e4530_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pestana Carlton Madeira Ocean Resort Hotel $1,293 per person Jun 7 - Jun 10 found 1 day ago Roundtrip non-stop flight included New York (NYC) to Funchal (FNC) 8.8/10 Excellent! (1,001 reviews) Gym could have had a rowing machine Reviewed on Apr 2, 2026 ![Pestana Casino Park Ocean and SPA Hotel](https://images.trvl-media.com/lodging/1000000/20000/14400/14349/b10be447_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pestana Casino Park Ocean and SPA Hotel $1,741 per person May 21 - May 24 found 1 hour ago Roundtrip non-stop flight included Boston (BOS) to Funchal (FNC) 8.6/10 Excellent! (1,002 reviews) The mountain view and Ocean views were impressive. Excellent service, food, great waiters - the best and so neat the city centre. Beautiful hotel and staff. Clean and great facilities with infinity pool and spa. Reviewed on Mar 25, 2026 ![Pestana Fisherman Village](https://images.trvl-media.com/lodging/69000000/68610000/68601600/68601519/w2800h1862x0y3-92403779_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pestana Fisherman Village $1,745 per person May 21 - May 24 found 1 hour ago Roundtrip non-stop flight included Boston (BOS) to Funchal (FNC) 9/10 Wonderful! (50 reviews) Amazing staff, great rooms but a little dark, guys breakfast. Reviewed on Jan 16, 2026 Don't see what you're looking for? See all available trips from Columbus to Madeira Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-04/2026-05-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=FNC&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Planning your Madeira Island ski vacation #### 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 $1,201\. 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 $1,201\. 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. 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](https://expedia.com/Madeira-Island-Vacation-Rentals.d11326.Travel-Guide-VacationRentals)[ Car Rentals in Madeira Island ](https://expedia.com/Car-Rentals-In-Madeira-Island.d11326.Car-Rental-Guide)[ Madeira Island Vacations ](https://expedia.com/Madeira-Island.d11326.Destination-Travel-Guides)[ Things to do in Madeira Island ](https://expedia.com/Things-To-Do-In-Madeira-Island.d11326.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app