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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 22 - Sep 25

    Vineyard Harbor Motel - Private Beach + Flight

    Vineyard Haven
    3 nights
    2.5 star property
    9.0/10 - Wonderful (697 reviews)
    "Spencer the property manager was very helpful"
    Reviewed July 22, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - BOS • Nonstop BOS - ATL • Nonstop
    $814
    $632
    per traveler
    found 1 day ago
    Vineyard Harbor Motel - Private Beach
  • Exterior
    Aug 21 - Aug 24

    The Franklin Hotel Martha's Vineyard + Flight

    Edgartown
    3 nights
    2.0 star property
    9.2/10 - Wonderful (198 reviews)
    "We truly enjoyed our stay at The Franklin. The location was great, the spaces were clean and well maintained, the staff was helpful and courteous, and the room was pleasant and comfortable. The common kitchen space was convenient and a great feature. A few small nit picky things: The bathroom door in our room was not aligned properly so it was difficult to close and made quite a bit of noise, which was disturbing to a partner sleeping. Likewise, the french door leading to the rear patio on the..."
    Reviewed July 21, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - MVY • 1 stop MVY - ATL • 1 stop
    Save 100% on your flight
    $1,818
    $1,376
    per traveler
    found 2 days ago
    The Franklin Hotel Martha's Vineyard
  • Lobby
    Aug 28 - Aug 31

    Morgan Hotel + Flight

    Oak Bluffs
    3 nights
    2.5 star property
    8.6/10 - Excellent (240 reviews)
    "I enjoyed the Morgan Hotel in which the room and sheets were clean. There were plenty of towels to go to the beach. Lastly, there were friendly staff in the midst of the great location in the Oak Bluffs area."
    Reviewed July 21, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - MVY • 1 stop MVY - ATL • 1 stop
    Save 100% on your flight
    $1,475
    $1,133
    per traveler
    found 2 days ago
    Morgan Hotel
  • Premium bedding, in-room safe, blackout drapes
    Aug 21 - Aug 24

    The Richard, The Edgartown Collection + Flight

    Edgartown
    3 nights
    3.5 star property
    9.6/10 - Exceptional (192 reviews)
    "Great location. Clean, well maintained property. Nice staff. Our Queen bed room was comfortable but def cozy. We had a great stay."
    Reviewed July 22, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - MVY • 1 stop MVY - ATL • 1 stop
    Save 100% on your flight
    $2,002
    $1,613
    per traveler
    found 2 days ago
    The Richard, The Edgartown Collection
  • Deluxe Room, 1 King Bed | View from room
    Aug 28 - Aug 31

    The Sydney, The Edgartown Collection + Flight

    Edgartown
    3 nights
    3.5 star property
    9.4/10 - Exceptional (195 reviews)
    "Clean conveient. Breakfast very good but Rooms a little too small though."
    Reviewed July 19, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - MVY • 1 stop MVY - ATL • 1 stop
    Save 100% on your flight
    $1,748
    $1,430
    per traveler
    found 2 days ago
    The Sydney, The Edgartown Collection

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 $632. 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 $632. 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.