Thimble Islands Ski Holidays

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Top Ski holiday packages in Thimble Islands

Price found within the past 48 hours. Click for updated prices.
  • 4 Feb - 7 Feb

    JW Marriott Essex House New York + Flight

    Manhattan
    3 nights
    4.5 star property
    8.8/10 - Excellent (1,001 reviews)
    Return • Dublin (DUB) - New York (JFK)
    DUB - JFK • Direct JFK - DUB • 1 stop
    £1,267
    £828
    per traveller
    found 1 day ago
    JW Marriott Essex House New York
  • 20 Jan - 25 Jan

    The St. Regis New York + Flight

    Manhattan
    5 nights
    5.0 star property
    9.2/10 - Wonderful (295 reviews)
    "The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong"
    Reviewed November 6, 2026
    Return • Dublin (DUB) - New York (JFK)
    DUB - JFK • Direct JFK - DUB • 1 stop
    £3,590
    £1,975
    per traveller
    found 2 hours ago
    The St. Regis New York
  • 11 Jan - 17 Jan

    Topping Rose House + Flight

    Bridgehampton
    6 nights
    4.5 star property
    9.0/10 - Wonderful (165 reviews)
    Return • London (LON) - New York (JFK)
    LHR - JFK • Direct JFK - LHR • Direct
    £10,940
    £6,511
    per traveller
    found 6 hours ago
    Topping Rose House
  • 24 Dec - 28 Dec

    Eurostars The Chemists’ Club Hotel + Flight

    Manhattan
    4 nights
    4.0 star property
    9.4/10 - Exceptional (567 reviews)
    "Very convenient location. Good sized rooms."
    Reviewed November 9, 2026
    Return • London (LHR) - New York (JFK)
    LHR - JFK • Direct JFK - LHR • 1 stop
    £2,119
    £1,350
    per traveller
    found 1 day ago
    Eurostars The Chemists’ Club Hotel
  • 28 Dec - 1 Jan

    1 Hotel Central Park + Flight

    Manhattan
    4 nights
    5.0 star property
    9.0/10 - Wonderful (1,008 reviews)
    "Lovely hotel and great location. Loved it. I rated it good because I arrived early and as expected my room wasn't yet ready. No problem. I left my bags and asked that they be taken up when the room was ready. I came back much later in the day (after check in time) and room wasn't yet ready and my bags of course weren't taken up. When I expressed some frustration, the situation was immediately resolved. But, I still don't get the delay. They tried to make it up to me by leaving a bottle of..."
    Reviewed November 9, 2026
    Return • Edinburgh (EDI) - New York (JFK)
    EDI - JFK • Direct JFK - EDI • 1 stop
    £3,006
    £2,053
    per traveller
    found 7 hours ago
    1 Hotel Central Park

Planning your Thimble Islands ski holiday

How can I book the best ski holiday to Thimble Islands in 2026/2027?

Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Thimble Islands. 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 Thimble Islands ski holidays?

Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Thimble Islands 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 £828. Prices and availability are subject to change. Additional terms may apply.

Can I book last-minute ski holidays to Thimble Islands?

Use our handy last-minute deals page to look for ski holidays to Thimble Islands 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 Thimble Islands?

Thimble Islands 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 Thimble Islands?

All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Thimble Islands. 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 Thimble Islands?

Ski season in Thimble Islands 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 Thimble Islands 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 Thimble Islands 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 Thimble Islands that offer it.

Why should I book a ski holiday package in Thimble Islands 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.