Title: Upcountry Maui Ski Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/507525/451f5c7a-2ae1-4683-8787-8d1827405b60.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Upcountry Maui Ski Holidays ## Book a Ski Hotel + Flight or Car together to unlock savings Photo by Project Forever - ## Plan, book, travel with confidence - ### Better together Save up to £335 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 Packages with flights are ATOL protected ## Top flight + Ski hotel deals in Upcountry Maui Price found within the past 48 hours. Click for updated prices. ![Royal Lahaina Resort & Bungalows](https://images.trvl-media.com/lodging/1000000/40000/34800/34767/96220cd0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Royal Lahaina Resort & Bungalows £1,524 per person 12 May - 18 May found 1 day ago Return flight included London (LGW) to Kahului (OGG) 8.6/10 Excellent! (1,713 reviews) Gretchen took care of us when ever we needed anything. Her amazing ability to make us feel like family was top notch. Reviewed on 29 Mar 2026 ![Sheraton Maui Resort & Spa](https://images.trvl-media.com/lodging/1000000/30000/22900/22894/d0dd58aa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sheraton Maui Resort & Spa £2,015 per person 12 May - 18 May found 1 day ago Return flight included London (LGW) to Kahului (OGG) 8.8/10 Excellent! (1,022 reviews) The staff was exceptional, so nice and patient. The location was very convenient to shops and great restaurants as well as beach access. It would be great if the hotel had a lifeguard on duty for the beach area. The grounds keep was good but could be a little better. The halls were a bit dirty but the outside areas were clean. The pool was great and large enough to separate from crowds. The restaurants and bars had great food for average cost. Drinks are a bit pricey but expected at resorts. Overall we had a great time and would definitely stay here again! Reviewed on 26 Mar 2026 ![Hotel Wailea, Relais & Chateaux - Adults Only](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/d048b5ef_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Wailea, Relais & Chateaux - Adults Only Wailea £2,611 per person 27 May - 29 May found 21 hours ago Return flight included London (STN) to Kahului (OGG) 9.4/10 Exceptional! (1,001 reviews) Literally the best hotel experience I’ve had. Reviewed on 21 Mar 2026 ![Ho‘olei Villas at Grand Wailea](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/3bd64cf1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ho‘olei Villas at Grand Wailea Wailea £3,844 per person 27 May - 29 May found 21 hours ago Return flight included London (STN) to Kahului (OGG) 9.6/10 Exceptional! (45 reviews) Womderful home, terrific service, access to hotel amenities was key. Reviewed on 28 Feb 2026 ![Wailea Beach Villas WBV-PH 412 by KBM](https://images.trvl-media.com/lodging/102000000/101130000/101120500/101120445/fe74a667_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wailea Beach Villas WBV-PH 412 by KBM Wailea £5,166 per person 27 May - 29 May found 21 hours ago Return flight included London (STN) to Kahului (OGG) No reviews Don't see what you're looking for? See all available trips from London to Upcountry Maui [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=LGW&Destination=OGG&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski holidays in Upcountry Maui Price found within the past 48 hours. Click for updated prices. ![Hotel Wailea, Relais & Chateaux - Adults Only](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/d048b5ef_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Wailea, Relais & Chateaux - Adults Only Wailea £2,611 per person 27 May - 29 May found 21 hours ago Return flight included London (STN) to Kahului (OGG) 9.4/10 Exceptional! (1,001 reviews) Literally the best hotel experience I’ve had. Reviewed on 21 Mar 2026 ![Ho‘olei Villas at Grand Wailea](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/3bd64cf1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ho‘olei Villas at Grand Wailea Wailea £3,844 per person 27 May - 29 May found 21 hours ago Return flight included London (STN) to Kahului (OGG) 9.6/10 Exceptional! (45 reviews) Womderful home, terrific service, access to hotel amenities was key. Reviewed on 28 Feb 2026 ![Fairmont Kea Lani Maui](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/299cd4dc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Kea Lani Maui Wailea £2,947 per person 27 May - 29 May found 21 hours ago Return flight included London (STN) to Kahului (OGG) 9.4/10 Exceptional! (1,012 reviews) Staff was incredibly welcoming and helpful. Bar/restaurant staff were amazing. Pools were clean and poolside servers were very friendly. Overall an amazing property with wonderful staff Reviewed on 16 Mar 2026 Don't see what you're looking for? See all available trips from London to Upcountry Maui [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=STN&Destination=OGG&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski holidays in Upcountry Maui Price found within the past 48 hours. Click for updated prices. ![Palms at Wailea Maui](https://images.trvl-media.com/lodging/1000000/20000/13100/13093/dc691bca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Palms at Wailea Maui Wailea £2,482 per person 27 May - 29 May found 21 hours ago Return flight included London (STN) to Kahului (OGG) 8.4/10 Very Good! (527 reviews) Very clean and modern condo. Very well maintained. Check in was a breeze and we loved the patio. Great location on the property. Reviewed on 12 Mar 2026 ![Hotel Wailea, Relais & Chateaux - Adults Only](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/d048b5ef_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Wailea, Relais & Chateaux - Adults Only Wailea £2,611 per person 27 May - 29 May found 21 hours ago Return flight included London (STN) to Kahului (OGG) 9.4/10 Exceptional! (1,001 reviews) Literally the best hotel experience I’ve had. Reviewed on 21 Mar 2026 ![Ho‘olei Villas at Grand Wailea](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/3bd64cf1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ho‘olei Villas at Grand Wailea Wailea £3,844 per person 27 May - 29 May found 21 hours ago Return flight included London (STN) to Kahului (OGG) 9.6/10 Exceptional! (45 reviews) Womderful home, terrific service, access to hotel amenities was key. Reviewed on 28 Feb 2026 Don't see what you're looking for? See all available trips from London to Upcountry Maui [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=STN&Destination=OGG&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Planning your Upcountry Maui ski holiday #### How can I book the best ski holiday to Upcountry Maui in 2026/2027? Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Upcountry Maui. Just choose your dates and see what’s available. You might prefer a hotel with a heated outdoor pool, or a private chalet for après ski parties; either way, use the property filters to your ideal match. If ski-in-ski-out is important, use the map view to find those idyllic slopeside properties. #### How can I find cheap Upcountry Maui ski holidays? Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Upcountry Maui accommodation a little further from the lifts and go self-catering to cut back on eating out. Sort your search results by price to find options from £1,524\. Prices and availability are subject to change. Additional terms may apply. #### Can I book last-minute ski holidays to Upcountry Maui? Use our handy last-minute deals page to look for ski holidays to Upcountry Maui at a steal. If your dates are fixed, simply input the details and see what specials are available. #### What should I consider when booking family ski holidays in Upcountry Maui? Upcountry Maui is well set up for kids. For the teeniest ski-woks, day care in the snow is a blast. As they get older, they love whizzing around on the hill in ski school. Choose a hotel near the lifts and nursery slopes to save a whole lot of ski-carrying hassle in the mornings. With all that extra time and energy, you can take your sweet time to find a family-favourite bolthole on the mountain for hot chocolate with marshmallows ski breaks. #### Can I book all-inclusive ski holidays to Upcountry Maui? All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Upcountry Maui. If not, consider booking your flights and accommodation together to save money that way instead. #### When's the best time of year to plan a ski trip to Upcountry Maui? Ski season in Upcountry Maui generally starts around December and slopes off around April. Keep an eye on the snow forecasts though, as you can often find some brilliant deals at the start or end of the season, when it’s also much quieter. #### How can I find the best deals on Upcountry Maui ski holiday packages? If you can be flexible with your ski holiday dates, avoid school holidays and instead buckle up your boots at the start or end of season. Sort your search results by price and look out for self-catered accommodation to save on notoriously expensive ski-resort drinking and dining. #### Can I book a Upcountry Maui ski trip with free cancellation and/or flexible dates? If you’re not 100% sure on plans or just want peace of mind, choose a ski holiday with free cancellation. You can use our free cancellation filter to find properties in Upcountry Maui that offer it. #### Why should I book a ski holiday package in Upcountry Maui with Expedia? Schuss your way to the slopes with Expedia’s smooth booking process. From flights to hotels and even car hire, you’ll find everything you need to plan the ultimate winter wonderland ski holiday. ## More holidays you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holiday packages](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ### Top Ski Holiday Destinations > - 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Savings not available on all packages. Flight-inclusive packages are ATOL protected. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in 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