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.
  • Jan 28 - Jan 31

    Holiday Inn Express & Suites Norwood-Boston Area by IHG + Flight

    Norwood
    3 nights
    3.0 star property
    8.4/10 - Very good (1,008 reviews)
    "All was great except for the fire alarm going off twice in the same evening! We were told the first time was for someone smoking in their room and the second time was from a faulty security box. Thank goodness it didn't happen again and the fire chief was still onsite. Great location, friendly staff, and clean rooms without carpet is a huge plus!"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $705
    CA $656
    per traveller
    found 6 hours ago
    Holiday Inn Express & Suites Norwood-Boston Area by IHG
  • Dec 29 - Jan 3

    Renaissance® Boston Seaport District + Flight

    Seaport District
    5 nights
    4.0 star property
    9.0/10 - Wonderful (1,008 reviews)
    "We went there on a Saturday night for the Halloween cruise came back at 9:30 PM with a knock at the door 10 minutes later telling us we could not have our music own. It was a small speaker not that loud. You have to pay parking, which I believe was $45 and not allowed to bring in any outside alcohol so you could only buy at the bar inside, which was expensive. The place was convenient clean but the elevators were so backed up with only two working over 30 minutes just to get up to our room."
    Reviewed November 9, 2026
    Roundtrip • Ottawa (YOW) - Boston (BOS)
    YOW - BOS • Nonstop BOS - YOW • Nonstop
    CA $1,315
    CA $1,095
    per traveller
    found 1 day ago
    Renaissance® Boston Seaport District
  • Dec 15 - Dec 18

    The Wylie Inn and Conference Center at Endicott College + Flight

    Beverly
    3 nights
    3.5 star property
    9.2/10 - Wonderful (1,254 reviews)
    Roundtrip • Ottawa (YOW) - Boston (BOS)
    YOW - BOS • 1 stop BOS - YOW • 1 stop
    CA $824
    CA $739
    per traveller
    found 1 day ago
    The Wylie Inn and Conference Center at Endicott College
  • Jan 28 - Jan 31

    Comfort Inn - Dedham-Boston MetroWest + Flight

    Dedham
    3 nights
    2.5 star property
    8.0/10 - Very good (105 reviews)
    "Shampoo and rinse were bit cheap. Soap was too cheap. Bath towel has somebody’s hair."
    Reviewed November 7, 2026
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $722
    CA $685
    per traveller
    found 6 hours ago
    Comfort Inn - Dedham-Boston MetroWest
  • Dec 15 - Dec 18

    Homewood Suites by Hilton Boston/Billerica + Flight

    Billerica
    3 nights
    3.0 star property
    7.8/10 - Good (1,005 reviews)
    "The room was large, with a king bed and a queen pull out, full kitchen with stove and fridge, and 2 televisions. The gym was enough, a pelton (which I could not get to work), a sit down bike, 2 treadmills, and an eliptical. It also had medicine balls, dumbbells, and yoga mats. The pool was very warm, if that's your thing! The breakfast was very good, ranging from eggs, sausage, pancakes, french toast sticks, bagels, toast, oj, apple juice, cereal..etc. There is something for everyone. The staff..."
    Reviewed November 9, 2026
    Roundtrip • Ottawa (YOW) - Boston (BOS)
    YOW - BOS • 1 stop BOS - YOW • 1 stop
    CA $820
    CA $780
    per traveller
    found 1 day ago
    Homewood Suites by Hilton Boston/Billerica

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.

Plan the ultimate ski vacation in Massachusetts

What are some benefits when booking ski vacations in Massachusetts?

If you're interested in skiing, there's nothing quite like a ski vacation. These trips are designed to allow you to enjoy being on the slopes and relax in tranquil and convenient accommodations at the end of the day. Amenities on ski trips can be pretty upscale, so it's easy to relax in a hot tub or at a spa in between your skiing excursions. Plus, they can put you right next to the slopes. You'll even find a variety of different vacation types available whether you're looking for family friendly, cheap, or even last minute ski vacations.

How can I book the best ski vacation in Massachusetts?

It is most important to implement the ski filter in your search when trying to find a ski vacation that will make you happy. Using the filter will automatically remove any entries that don't offer the skiing opportunities you want. After that, you'll need to think about what specifically you want from Massachusetts, and think about the time of year that's best to visit.

How can I find cheap ski vacations?

Cheap ski vacations are readily available in Massachusetts with some as cheap as CA $656. You can see the cheapest options by sorting your accommodation choices by price, which automatically puts the least-expensive results at the top of the list. You may also want to consider an accommodation with a kitchen, so you can cook instead of eating out.

Can I book ski packages?

Yes, ski packages are readily available throughout Massachusetts. All you have to do is put in your travel dates and see what's available. When you book a ski package, you may be able to enjoy discounts with savings of up to 7 when you book your accommodation and your flight together.

What should I consider when booking family ski vacations?

The key to a successful family ski vacation is ensuring that your family is kept happy and entertained. Consider what your family members are interested in and the kind of vacation they want. If they have little skiing experience, for example, you may want to opt for an accommodation that offers ski lessons or a kid's club. Various slope difficulties may be essential in providing opportunities for everyone at Massachusetts.

Can I book all-inclusive ski vacations in Massachusetts?

Yes, all-inclusive ski trips are available and may be precisely what you're looking for. All you have to do is include the filter for all-inclusive stays, and your search results will only show the accommodations that provide this handy feature that allows you to plan your entire trip to Massachusetts in advance.

What's the best time of year to plan a ski trip?

The apparent answer to when you should plan a ski trip is in winter, but other details are important too. If you book for Massachusetts's high season around January and February, you'll likely find increased prices. It's generally best to opt for the early or late season in December and April, as prices tend not to be quite as high.

How can I find the best deals on ski packages in Massachusetts?

When you're looking for cheap ski vacations, there are a few factors you can take advantage of to help get the best deals. Travelling during the off-season can be cheaper since there's more availability. However, the beginning and end of the season tend to be the most affordable for skiing.

Can I book a ski vacation that's fully refundable?

Being fully refundable is a feature you'll find on several accommodation packages in Massachusetts. You can even search for it explicitly using a filter for full refundability.

Why should I book a ski vacation package with Expedia?

When you book with Expedia, you'll find everything you need for cheap ski vacations, luxury ski vacations and everything in between in one central location. You may even be able to enjoy discounts for booking your accommodation and your flight together with savings of up to 7. With Expedia Rewards, you can earn points towards your next booking.