Great Diamond Island Ski Vacations

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Top Ski vacation packages in Great Diamond Island

Price found within the past 48 hours. Click for updated prices.
84 Main

84 Main

$617
per person
Nov 19 - Nov 22
found 19 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.8/10 Exceptional! (58 reviews)
The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.

Reviewed on Jul 17, 2026

Cliff House Maine

Cliff House Maine

Bald Head
Save 100% on your flight
$1,166
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
Portland Harbor Hotel

Portland Harbor Hotel

Downtown Portland
$870
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.2/10 Wonderful! (1,864 reviews)
Inn By The Sea

Inn By The Sea

$1,233
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (333 reviews)
The Weldon Hotel

The Weldon Hotel

Downtown Portland
$1,227
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.8/10 Exceptional! (119 reviews)
Incre

Reviewed on Oct 4, 2026

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5* Ski vacations in Great Diamond Island

Price found within the past 48 hours. Click for updated prices.
White Barn Inn & Spa, Auberge Collection

White Barn Inn & Spa, Auberge Collection

$1,199
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.6/10 Exceptional! (124 reviews)
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3 Night Ski vacations in Great Diamond Island

Price found within the past 48 hours. Click for updated prices.
84 Main

84 Main

$617
per person
Nov 19 - Nov 22
found 19 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.8/10 Exceptional! (58 reviews)
The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.

Reviewed on Jul 17, 2026

Cliff House Maine

Cliff House Maine

Bald Head
Save 100% on your flight
$1,166
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
Inn By The Sea

Inn By The Sea

$814
per person
Nov 19 - Nov 22
found 19 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (333 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Great Diamond Island
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4 Night Ski vacations in Great Diamond Island

Price found within the past 48 hours. Click for updated prices.
The Meadowmere Resort

The Meadowmere Resort

$741
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
8.6/10 Excellent! (1,008 reviews)
Good location. New Reno’s were very nice! Helpful staff.

Reviewed on Oct 5, 2026

Evalina Hotel

Evalina Hotel

Downtown Portland
$1,231
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
10/10 Exceptional! (13 reviews)
Centrally located in the Old Port, with views of the harbor, this was a last minute — therefore pricey — excellent find for a fall weekend getaway. Stylish, elegant rehab of 19th century granite industrial building. Whimsical decor notes referring to 19th century owner Evalina Fox. Nicely appointed kitchenette — though if you came to Portland for the foodie scene, you might end up just using it for breakfast, as we did. Only sour note was the disco music (coming in via the ventilation system?) from a nearby establishment audible during business hours. Well, if you pick a hotel in the middle of things, you get the noise and bustle that comes from being in the middle of things. That said, we’d come again, but shoot for a penthouse/upper floor unit farther from the street-level mania.

Reviewed on Oct 5, 2026

The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

Downtown Portland
$1,305
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
9.6/10 Exceptional! (70 reviews)
This place is gorgeous! I highly recommend it. Beautiful modern design with everything you might need. Great central location. A bit hard to find. Parking was A lot! But made life easier. Will stay here again.

Reviewed on Oct 6, 2026

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Planning your Great Diamond Island ski vacation

What are some things I should consider when booking a Great Diamond 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 Great Diamond Island ski packages?

Right now, ski trips start at just $617. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Great Diamond Island?

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Great Diamond 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 Great Diamond Island cost?

Sensational ski trips to Great Diamond Island start from $617. 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 Great Diamond Island?

The best time to hit the slopes in Great Diamond 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 Great Diamond 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 Great Diamond 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 Great Diamond Island with Expedia?

Simple search and fantastic filters make it easy to find, build, and book your dream Great Diamond Island ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.

Things to do

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

$77
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland: Casco Bay Morning Lighthouse Cruise

Portland: Casco Bay Morning Lighthouse Cruise

$59
per adult
80% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
Sunset Lighthouse Cruise Along Casco Bay

Sunset Lighthouse Cruise Along Casco Bay

$69
per adult
Sunset Lighthouse Cruise Along Casco Bay
See all activities in Great Diamond Island

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.