Portland Ski Holidays

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Planning your Portland ski holiday

How can I book the best ski holiday to Portland in 2025/2026?

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

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

Can I book last-minute ski holidays to Portland?

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

Portland 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 Portland?

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

Ski season in Portland 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 Portland 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 Portland 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 Portland that offer it.

Why should I book a ski holiday package in Portland 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.

Top Ski Portland Hotels

Embassy Suites by Hilton Portland Maine
Embassy Suites by Hilton Portland Maine
3.5 out of 5
1050 Westbrook Street, Portland, ME
  • 25 min walk from Thompson's Point
Stay at this business-friendly hotel in Portland. Enjoy free breakfast, free Wi-Fi and a free airport shuttle. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (1,116 reviews)
Exceptional Stay!!
"Made a last minute reservation on Hotels.com due to a flight cancelation. Was greeted warmly and checked in promptly at the hotel. The facility was obviously recently renovated and beautiful. The rooms were in new condition also. This was a very nice surprise. Enjoyed free happy hour cocktails and ..."

Reviewed on 3 Jul 2025

Embassy Suites by Hilton Portland Maine
Kennebunkport Inn
Kennebunkport Inn
3 out of 5
One Dock Square, Kennebunkport, ME
  • 55 min drive from Thompson's Point
Stay at this 3-star hotel in Kennebunkport. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular ...
9/10 Wonderful! (526 reviews)
"Perfect spot for a solo trip. Loved every moment and will definitely return. The staff is lovely, gracious, and always smiling"

Reviewed on 2 Jul 2025

Kennebunkport Inn
Oceanfront condo!!!!  Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Old Orchard Beach, ME
  • 26 min drive from Thompson's Point
Stay at this beach condo in Old Orchard Beach. Enjoy free Wi-Fi, a beach locale and a water park. Popular attractions Old Orchard Beach and Old Orchard Beach ...
9.6/10 Exceptional! (204 reviews)
Sister trip
"Excellent location! Beautiful views from the deck. Love that we can hear the ocean inside the condo! The bands provide entertainment. Already have another visit booked!!"

Reviewed on 2 Jul 2025

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.