Massachusetts Ski Holidays

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4 Night Ski holidays in Massachusetts

Price found within the past 48 hours. Click for updated prices.
Westford Regency Inn & Conference Center
Homewood Suites by Hilton Boston/Canton, MA
Residence Inn Boston Dedham
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Planning your Massachusetts ski holiday

How can I book the best ski holiday to Massachusetts in 2025/2026?

Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Massachusetts. Just choose your dates and see what’s available. You might prefer a hotel with a heated outdoor pool, or a private chalet for après ski parties; either way, use the property filters to your ideal match. If ski-in-ski-out is important, use the map view to find those idyllic slopeside properties.

How can I find cheap Massachusetts ski holidays?

Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Massachusetts accommodation a little further from the lifts and go self-catering to cut back on eating out. Sort your search results by price to find options from £601. Prices and availability are subject to change. Additional terms may apply.

Can I book last-minute ski holidays to Massachusetts?

Use our handy last-minute deals page to look for ski holidays to Massachusetts at a steal. If your dates are fixed, simply input the details and see what specials are available.

What should I consider when booking family ski holidays in Massachusetts?

Massachusetts is well set up for kids. For the teeniest ski-woks, day care in the snow is a blast. As they get older, they love whizzing around on the hill in ski school. Choose a hotel near the lifts and nursery slopes to save a whole lot of ski-carrying hassle in the mornings. With all that extra time and energy, you can take your sweet time to find a family-favourite bolthole on the mountain for hot chocolate with marshmallows ski breaks.

Can I book all-inclusive ski holidays to Massachusetts?

All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Massachusetts. If not, consider booking your flights and accommodation together to save money that way instead.

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

Ski season in Massachusetts generally starts around December and slopes off around April. Keep an eye on the snow forecasts though, as you can often find some brilliant deals at the start or end of the season, when it’s also much quieter.

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

If you can be flexible with your ski holiday dates, avoid school holidays and instead buckle up your boots at the start or end of season. Sort your search results by price and look out for self-catered accommodation to save on notoriously expensive ski-resort drinking and dining.

Can I book a Massachusetts ski trip with free cancellation and/or flexible dates?

If you’re not 100% sure on plans or just want peace of mind, choose a ski holiday with free cancellation. You can use our free cancellation filter to find properties in Massachusetts that offer it.

Why should I book a ski holiday package in Massachusetts with Expedia?

Schuss your way to the slopes with Expedia’s smooth booking process. From flights to hotels and even car hire, you’ll find everything you need to plan the ultimate winter wonderland ski holiday.

Top Ski Massachusetts Hotels

The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
  • 13 min drive from Fenway Park
The price is £131 per night from 13 Jul to 14 Jul
£131
13 Jul - 14 Jul
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
9/10 Wonderful! (1,006 reviews)
"All was fine!"

Reviewed on 30 Jun 2025

The Yankee, Trademark Collection by Wyndham
Berkshire Valley Inn
Berkshire Valley Inn
2.5 out of 5
2541 Hancock Rd, Williamstown, MA
  • 14 min drive from Fenway Park
The price is £129 per night from 31 Jul to 1 Aug
£129
31 Jul - 1 Aug
includes taxes & fees
Stay at this hotel in Williamstown. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. ...
9/10 Wonderful! (549 reviews)
"Beautiful property, wonderful staff, great breakfast."

Reviewed on 23 Jun 2025

Berkshire Valley Inn
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3 out of 5
37 Corey Rd, Hancock, MA
The price is £145 per night from 7 Jul to 8 Jul
£145
7 Jul - 8 Jul
includes taxes & fees
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants and 2 bars/lounges. Our guests praise the property condition in their reviews. Popular ...
8.2/10 Very Good! (943 reviews)
"Beautiful setting. Friendly staff."

Reviewed on 30 Jun 2025

Jiminy Peak Mountain Resort
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.