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A coastal landscape with a sandy beach, grassy areas, and a small island with a lighthouse.

Cuttyhunk Ski Vacations

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Top Ski vacation packages in Cuttyhunk

Price found within the past 48 hours. Click for updated prices.
  • Courtyard view
    Sep 7 - Sep 11

    Vineyard Harbor Motel - Private Beach + Flight

    Vineyard Haven
    4 nights
    2.5 star property
    9.0/10 - Wonderful (715 reviews)
    "Cute hotel within a verry short walking distance from the ferry terminal and bus stop. Very clean, refrigerator in the room, good water pressure and hot water. There was a nice lounge area with a washer and dryer. Couldn't find an ice machine (didn't look hard either) and there was no full length mirror in the room but that was the only downside. Nice private beach area and deck overlooking the water. There is a grocery store across the street and down a block which was very nice to have close..."
    Reviewed August 3, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - BOS • Nonstop BOS - ATL • Nonstop
    $1,183
    $1,036
    per traveler
    found 1 day ago
    Vineyard Harbor Motel - Private Beach
  • Exterior
    Sep 7 - Sep 11

    The Franklin Hotel Martha's Vineyard + Flight

    Edgartown
    4 nights
    2.0 star property
    9.2/10 - Wonderful (199 reviews)
    "Sweet place"
    Reviewed July 27, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - BOS • Nonstop BOS - ATL • Nonstop
    $1,312
    $1,099
    per traveler
    found 1 day ago
    The Franklin Hotel Martha's Vineyard
  • Condo | Laptop workspace, WiFi (free), individually decorated
    Sep 7 - Sep 11

    The Island Inn on Martha's Vineyard + Flight

    Oak Bluffs
    4 nights
    2.5 star property
    8.4/10 - Very Good (42 reviews)
    "Great place, had a business trip and would stay again in the future."
    Reviewed August 3, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - BOS • Nonstop BOS - ATL • Nonstop
    $1,540
    $1,322
    per traveler
    found 1 day ago
    The Island Inn on Martha's Vineyard
  • Premium bedding, in-room safe, blackout drapes
    Sep 7 - Sep 11

    The Richard, The Edgartown Collection + Flight

    Edgartown
    4 nights
    3.5 star property
    9.6/10 - Exceptional (193 reviews)
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - BOS • Nonstop BOS - ATL • Nonstop
    $1,609
    $1,393
    per traveler
    found 1 day ago
    The Richard, The Edgartown Collection
  • Lobby
    Sep 7 - Sep 11

    Morgan Hotel + Flight

    Oak Bluffs
    4 nights
    2.5 star property
    8.6/10 - Excellent (247 reviews)
    "The lady at the front desk was amazing. I believe she was actually doing all the jobs."
    Reviewed August 3, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - BOS • Nonstop BOS - ATL • Nonstop
    $1,202
    $1,050
    per traveler
    found 1 day ago
    Morgan Hotel

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 $1,036. 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 $1,036. 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.