Cuttyhunk Ski Vacations 2026

Top Ski vacation packages in Cuttyhunk

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

Faraway Martha's Vineyard

$1,800

per person

Nov 30 - Dec 5

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Vineyard Haven (MVY)

9/10 Wonderful! (1,001 reviews)

Front desk staff was wonderful. Location is perfect. The bartender in the attached restaurant bar was so sweet!! Loved the pool even in October as well as the hot tub.

Reviewed on Oct 21, 2026

Harbor View Hotel

$1,984

per person

Nov 30 - Dec 5

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Loved the heated saltwater pool. Was disappointed there was not comfortable sitting in the room, esp on a rainy day or not feeling well, and watching a movie. Was surprised no elevator and we were on the third floor. The “grab and go” breakfast option was no more than a few pastries. That was disappointing. For early departure to catch ferry at 0530, no coffee was available.

Reviewed on Oct 22, 2026

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5* Ski vacations in Cuttyhunk

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

Harbor View Hotel

$1,984

per person

Nov 30 - Dec 5

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Reviewed on Oct 22, 2026

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4 Night Ski vacations in Cuttyhunk

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

The Franklin Hotel Martha's Vineyard

$1,127

per person

Dec 30 - Jan 3

found 11 hours ago

Roundtrip flight included

New York (NYC) to Vineyard Haven (MVY)

9.2/10 Wonderful! (215 reviews)

The Island Inn on Martha's Vineyard

$1,316

per person

Dec 30 - Jan 3

found 16 hours ago

Roundtrip flight included

New York (NYC) to Vineyard Haven (MVY)

8.2/10 Very Good! (58 reviews)

Vineyard Harbor Motel - Private Beach

$1,130

per person

Dec 30 - Jan 3

found 16 hours ago

Roundtrip flight included

New York (NYC) to Vineyard Haven (MVY)

9/10 Wonderful! (812 reviews)

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What are some things I should consider when booking a Cuttyhunk 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 Cuttyhunk ski packages?

Right now, ski trips start at just $1,127. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Cuttyhunk?

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

Sensational ski trips to Cuttyhunk start from $1,127. 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 Cuttyhunk?

The best time to hit the slopes in Cuttyhunk 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 Cuttyhunk 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 Cuttyhunk 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 Cuttyhunk with Expedia?

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