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.
  • A swimming pool with a tiled deck, lounge chairs, and large windows offering a view of the outdoors.
    Jan 15 - Jan 18

    Hampton Inn Boston/Braintree + Flight

    North Braintree
    3 nights
    3.0 star property
    8.4/10 - Very good (1,044 reviews)
    "Awesome"
    Reviewed November 5, 2026
    Roundtrip • Los Angeles (LAX) - Boston (BOS)
    LAX - BOS • Nonstop BOS - LAX • Nonstop
    $523
    $476
    per traveler
    found 1 day ago
    Hampton Inn Boston/Braintree
  • A coastal scene with a sandy beach, rocky outcrops, and a lighthouse in the distance.
    Dec 18 - Dec 21

    The Wylie Inn and Conference Center at Endicott College + Flight

    Beverly
    3 nights
    3.5 star property
    9.2/10 - Wonderful (1,247 reviews)
    Roundtrip • Dallas (DFW) - Boston (BOS)
    DFW - BOS • Nonstop BOS - DFW • 1 stop
    $600
    $512
    per traveler
    found 1 day ago
    The Wylie Inn and Conference Center at Endicott College
  • A lobby with curved seating, a central circular design on the floor, and a reception desk with a marble counter.
    Dec 21 - Dec 26

    Renaissance® Boston Seaport District + Flight

    Seaport District
    5 nights
    4.0 star property
    9.0/10 - Wonderful (1,001 reviews)
    Roundtrip • Dallas (DFW) - Boston (BOS)
    DFW - BOS • Nonstop BOS - DFW • Nonstop
    $988
    $887
    per traveler
    found 1 day ago
    Renaissance® Boston Seaport District
  • A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.
    Jan 29 - Jan 31

    The Ellery + Flight

    Northampton
    2 nights
    3.5 star property
    9.4/10 - Exceptional (1,006 reviews)
    "The hotel was immaculate. The lobby was New England quaint. Our king sized mattress was extremely comfortable and the room was large. We will definitely return."
    Reviewed November 4, 2026
    Roundtrip • Dallas (DFW) - Boston (BOS)
    DAL - BOS • Nonstop BOS - DFW • 1 stop
    $543
    $523
    per traveler
    found 1 day ago
    The Ellery
  • A hotel with multiple buildings, a covered entrance, and a reflection in the water.
    Dec 18 - Dec 20

    Homewood Suites by Hilton Boston/Billerica + Flight

    Billerica
    2 nights
    3.0 star property
    7.8/10 - Good (1,003 reviews)
    "Easy access"
    Reviewed November 6, 2026
    Roundtrip • Dallas (DFW) - Boston (BOS)
    DFW - BOS • Nonstop BOS - DFW • 1 stop
    $507
    $492
    per traveler
    found 6 hours ago
    Homewood Suites by Hilton Boston/Billerica

Discover the most popular places to visit in Massachusetts

A cityscape with a prominent stadium, a busy intersection, and a skyline with high-rise buildings.

Fenway Park

9.2/10 (11,009 reviews)
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
See properties

What to do in Massachusetts

Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

$37
per adult
92% of travelers recommend
City Cruises Boston: Historic Sightseeing Cruise
See all activities in Massachusetts

Top Ski Massachusetts Hotels

A hotel dining area with multiple tables and chairs, a large window with curtains, and a hanging light fixture.

Hampton Inn & Suites Westford-Chelmsford

Hampton Inn & Suites Westford-Chelmsford
2.5 star property
11.6 mi from Massachusetts
8.8 out of 10, Excellent, (1,000 reviews)
"I was greeted warmly by the staff. The room was clean and well-appointed. I especially appreciated the many outlets all over the room and the bathroom as well as the charging pad near the bed. The breakfast was very good, plentiful and the staff was very attentive."
$110 nightly
The price is $122
Nov 15 - Nov 16
Total with taxes and fees
Hampton Inn & Suites Westford-Chelmsford
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.
See all properties in Massachusetts

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 $476. 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 $476. 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.