Cuttyhunk Ski Vacations

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Top Ski vacation packages in Cuttyhunk

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

Harbor View Hotel

$1,986
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
For a thousand a night I don’t expect to hear neighbors and televisions.

Reviewed on Sep 10, 2026

Faraway Martha's Vineyard

Faraway Martha's Vineyard

$2,165
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
The Faraway hotel in Edgartown is one of the nicest hotels on Martha's Vineyard. The location is unbeatable. They have their own parking lot which is key on the island. From the time you walk into the stunning lobby you are met by attentive staff and the hotels own signature fragrance. The rooms are spacious, updated and very clean. And the pool is an oasis in itself. I wouldn't stay anywhere else on the island.

Reviewed on Sep 8, 2026

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5* Ski vacations in Cuttyhunk

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

Harbor View Hotel

$1,986
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
For a thousand a night I don’t expect to hear neighbors and televisions.

Reviewed on Sep 10, 2026

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See all available trips from Columbus to Cuttyhunk
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3 Night Ski vacations in Cuttyhunk

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

Harbor View Hotel

$1,965
per person
Oct 16 - Oct 19
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
For a thousand a night I don’t expect to hear neighbors and televisions.

Reviewed on Sep 10, 2026

Faraway Martha's Vineyard

Faraway Martha's Vineyard

$2,154
per person
Oct 16 - Oct 19
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
The Faraway hotel in Edgartown is one of the nicest hotels on Martha's Vineyard. The location is unbeatable. They have their own parking lot which is key on the island. From the time you walk into the stunning lobby you are met by attentive staff and the hotels own signature fragrance. The rooms are spacious, updated and very clean. And the pool is an oasis in itself. I wouldn't stay anywhere else on the island.

Reviewed on Sep 8, 2026

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See all available trips from Columbus to Cuttyhunk
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4 Night Ski vacations in Cuttyhunk

Price found within the past 48 hours. Click for updated prices.
Faraway Martha's Vineyard

Faraway Martha's Vineyard

$1,526
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
The Faraway hotel in Edgartown is one of the nicest hotels on Martha's Vineyard. The location is unbeatable. They have their own parking lot which is key on the island. From the time you walk into the stunning lobby you are met by attentive staff and the hotels own signature fragrance. The rooms are spacious, updated and very clean. And the pool is an oasis in itself. I wouldn't stay anywhere else on the island.

Reviewed on Sep 8, 2026

Harbor View Hotel

Harbor View Hotel

$1,754
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
For a thousand a night I don’t expect to hear neighbors and televisions.

Reviewed on Sep 10, 2026

The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

$1,614
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Vineyard Haven (MVY)
8.4/10 Very Good! (53 reviews)
The worst place we stayed at. The bed was broken and we had to sleep on living room couch…the bathroom doors didn’t look and one bathroom door didn’t close. We complained to front desk in person next day but were not much help and didn’t even bother to change room forget about the upgrade for the inconvenience. It’s nice property but not being maintained by staff and staff not really there to help as they are just there to do minimum and collect their check!

Reviewed on Sep 10, 2026

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Planning your Cuttyhunk ski vacation

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 $1,526. 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 $1,526. 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.

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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.