A calm sea with a sailboat and rocky coastline.

Great Diamond Island Ski Holidays

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Top Ski holiday packages in Great Diamond Island

Price found within the past 48 hours. Click for updated prices.
  • 15 Dec - 19 Dec

    Holiday Inn Express Wells-Ogunquit-Kennebunk by IHG + Flight

    Wells
    4 nights
    3.0 star property
    9.2/10 - Wonderful (739 reviews)
    Return • Edinburgh (EDI) - Portland (PWM)
    EDI - BOS • 1 stop BOS - EDI • 1 stop
    £981
    £977
    per traveller
    found 1 day ago
    Holiday Inn Express Wells-Ogunquit-Kennebunk by IHG
  • 15 Dec - 19 Dec

    Dormir + Flight

    Windham
    4 nights
    3.0 star property
    9.0/10 - Wonderful (1,006 reviews)
    Return • Edinburgh (EDI) - Portland (PWM)
    EDI - BOS • 1 stop BOS - EDI • 1 stop
    £1,037
    £1,019
    per traveller
    found 1 day ago
    Dormir
  • 15 Dec - 19 Dec

    Holiday Inn Portland-By the Bay by IHG + Flight

    Downtown Portland
    4 nights
    4.0 star property
    9.0/10 - Wonderful (1,678 reviews)
    Return • Edinburgh (EDI) - Portland (PWM)
    EDI - BOS • 1 stop BOS - EDI • 1 stop
    £1,032
    £1,025
    per traveller
    found 1 day ago
    Holiday Inn Portland-By the Bay by IHG
  • 15 Dec - 19 Dec

    Holiday Inn Express Hotel & Suites Freeport by IHG + Flight

    Freeport
    4 nights
    2.5 star property
    8.8/10 - Excellent (1,000 reviews)
    "I was happy with everythingl"
    Reviewed October 28, 2026
    Return • Edinburgh (EDI) - Portland (PWM)
    EDI - BOS • 1 stop BOS - EDI • 1 stop
    £996
    £991
    per traveller
    found 1 day ago
    Holiday Inn Express Hotel & Suites Freeport by IHG
  • 15 Dec - 19 Dec

    Hampton Inn Kennebunk Kennebunkport + Flight

    Kennebunk
    4 nights
    2.5 star property
    9.4/10 - Exceptional (891 reviews)
    "Friendly staff. The room is clean and bed was comfortable. Great spot for the price. I had a super early meeting and really appreciated the grab and go bag breakfast because I didn’t have time to get to the buffet which was simple but good. Free water bottles offered to me when I checked in late was a nice touch."
    Reviewed November 4, 2026
    Return • Edinburgh (EDI) - Portland (PWM)
    EDI - BOS • 1 stop BOS - EDI • 1 stop
    £1,026
    £1,022
    per traveller
    found 1 day ago
    Hampton Inn Kennebunk Kennebunkport

Planning your Great Diamond Island ski holiday

How can I book the best ski holiday to Great Diamond Island in 2026/2027?

Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Great Diamond Island. 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 Great Diamond Island ski holidays?

Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Great Diamond Island 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 £977. Prices and availability are subject to change. Additional terms may apply.

Can I book last-minute ski holidays to Great Diamond Island?

Use our handy last-minute deals page to look for ski holidays to Great Diamond Island 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 Great Diamond Island?

Great Diamond Island 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 Great Diamond Island?

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

Ski season in Great Diamond Island 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 Great Diamond Island 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 Great Diamond Island 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 Great Diamond Island that offer it.

Why should I book a ski holiday package in Great Diamond Island 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.