Skip to main content
A coastal landscape with a sandy beach, grassy areas, and a small island with a lighthouse.

Cuttyhunk Ski Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Ski vacation packages in Cuttyhunk

Price found within the past 48 hours. Click for updated prices.
  • Courtyard view
    Aug 28 - Aug 31

    Vineyard Harbor Motel - Private Beach + Flight

    Vineyard Haven
    3 nights
    2.5 star property
    9.0/10 - Wonderful (688 reviews)
    "Location was good. The water had bacteria who couldn’t swim. Staff seemed to be a little stressed perhaps understaffed a bit. Couldn’t check until a little bit later. The toilet was not working properly or something."
    Reviewed July 18, 2026
    Roundtrip • Charlotte (CLT) - Vineyard Haven (MVY)
    CLT - BOS • Nonstop BOS - CLT • Nonstop
    $1,282
    $995
    per traveler
    found 1 day ago
    Vineyard Harbor Motel - Private Beach
  • Exterior
    Aug 28 - Aug 31

    The Franklin Hotel Martha's Vineyard + Flight

    Edgartown
    3 nights
    2.0 star property
    9.2/10 - Wonderful (197 reviews)
    "We had a great stay at the Franklin. It was a beautiful property and the design was well thought out. Great location and staff was kind and welcoming. Loved that they had beach chairs to use too! Will definitely be back."
    Reviewed July 19, 2026
    Roundtrip • Charlotte (CLT) - Vineyard Haven (MVY)
    CLT - BOS • Nonstop BOS - CLT • Nonstop
    Save 100% on your flight
    $1,861
    $1,432
    per traveler
    found 1 day ago
    The Franklin Hotel Martha's Vineyard
  • Lobby
    Oct 1 - Oct 5

    Morgan Hotel + Flight

    Oak Bluffs
    4 nights
    2.5 star property
    8.6/10 - Excellent (238 reviews)
    "The location is fantastic. Sure the rooms are small in size but it's a historic building and they make up for it in charm and comfort. The bed is so incredibly comfortable. Alicia was at the front desk and assisted with our check in. She was friendly, engaging and helpful in showing us all the great features of the hotel and offered suggestions for things to enjoy around town. I will definitely be staying here again."
    Reviewed July 13, 2026
    Roundtrip • Dallas (DFW) - Vineyard Haven (MVY)
    DFW - BOS • Nonstop BOS - DFW • 1 stop
    $1,412
    $1,132
    per traveler
    found 1 day ago
    Morgan Hotel
  • Premium bedding, in-room safe, blackout drapes
    Aug 28 - Aug 31

    The Richard, The Edgartown Collection + Flight

    Edgartown
    3 nights
    3.5 star property
    9.6/10 - Exceptional (190 reviews)
    Roundtrip • Charlotte (CLT) - Vineyard Haven (MVY)
    CLT - BOS • Nonstop BOS - CLT • Nonstop
    $1,908
    $1,562
    per traveler
    found 1 day ago
    The Richard, The Edgartown Collection
  • Terrace/patio
    Aug 28 - Aug 31

    The Edgartown Inn, The Edgartown Collection + Flight

    Edgartown
    3 nights
    3.5 star property
    9.8/10 - Exceptional (161 reviews)
    "Another Great stay at Edgartown Inn. Property very charming and perfect Location. Staff were incredible!!"
    Reviewed July 16, 2026
    Roundtrip • Charlotte (CLT) - Vineyard Haven (MVY)
    CLT - BOS • Nonstop BOS - CLT • Nonstop
    $2,474
    $2,161
    per traveler
    found 1 day ago
    The Edgartown Inn, 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 $995. 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 $995. 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.