A coastal village with houses, a lighthouse, and boats on the water.

Massachusetts Ski Vacations

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Top Ski vacation packages in Massachusetts

Price found within the past 48 hours. Click for updated prices.
  • Oct 1 - Oct 4

    Hampton Inn Boston/Braintree + Flight

    North Braintree
    3 nights
    3.0 star property
    8.2/10 - Very Good (1,004 reviews)
    Roundtrip Chicago (CHI) - Boston (BOS)
    ORD - BOSNonstop BOS - ORDNonstop
    $664
    $547
    per traveler
    found 12 hours ago
    Hampton Inn Boston/Braintree
  • Aug 25 - Aug 28

    The Wylie Inn and Conference Center at Endicott College + Flight

    Beverly
    3 nights
    3.5 star property
    9.2/10 - Wonderful (1,177 reviews)
    "Very clean hotel and rooms. Great hotel bar and shout out to Karen, a great bartender. Gym was also very updated and not a lot of equipment but useful nonetheless. Rooms are very very very small but comfy bed and clean. Would definitely recommend."
    Reviewed July 16, 2026
    Roundtrip Burbank (BUR) - Boston (BOS)
    BUR - BOS1 stop BOS - BUR1 stop
    $721
    $557
    per traveler
    found 2 hours ago
    The Wylie Inn and Conference Center at Endicott College
  • Aug 31 - Sep 5

    Frederick William House + Flight

    Falmouth
    5 nights
    3.5 star property
    9.6/10 - Exceptional (317 reviews)
    "I absolutely loved the property! Beautiful, clean and serene. I highly recommend. So happy with our visit."
    Reviewed July 10, 2026
    Roundtrip Chicago (CHI) - Boston (BOS)
    ORD - MVY1 stop MVY - RFD1 stop
    $1,323
    $1,093
    per traveler
    found 12 hours ago
    Frederick William House
  • Aug 20 - Aug 24

    Chapter House + Flight

    Yarmouth Port
    4 nights
    3.5 star property
    9.2/10 - Wonderful (176 reviews)
    "Lovely property in a quiet area of Cape Cod. A few shops within walking distance and a twenty minute drive from the shops of Chatham. Nice grounds. The floor of the room was a bit grimy."
    Reviewed July 11, 2026
    Roundtrip Chicago (CHI) - Hyannis (HYA)
    ORD - ACK1 stop ACK - ORD1 stop
    $1,100
    $962
    per traveler
    found 1 day ago
    Chapter House
  • Oct 5 - Oct 10

    DoubleTree by Hilton Hotel Boston - Westborough + Flight

    Westborough
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,007 reviews)
    Roundtrip Dallas (DFW) - Boston (BOS)
    DFW - BOS1 stop BOS - DFW1 stop
    $776
    $692
    per traveler
    found 1 day ago
    DoubleTree by Hilton Hotel Boston - Westborough

Discover the most popular places to visit in Massachusetts

What to do in Massachusetts

Top Ski Massachusetts Hotels

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Planning your Massachusetts ski vacation

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

Right now, ski trips start at just $547. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Massachusetts?

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

Sensational ski trips to Massachusetts start from $547. 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 Massachusetts?

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

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