Title: Massachusetts Ski Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/223/15b716aa-7bcd-4985-a9a4-b76daf9495af.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Massachusetts Ski Holidays ## Book a Ski Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £335 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 Packages with flights are ATOL protected ## Planning your Massachusetts ski holiday #### How can I book the best ski holiday to Massachusetts in 2026/2027? 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 . 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](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Yankee, Trademark Collection by Wyndham 461 Pittsfield Rd Lenox MA - 13 min drive from Fenway Park £81 9 Feb - 10 Feb 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! (1,005 reviews) Room was reasonably comfortable and always nice to be looking out at the mountain. Staff is always pleasant and efficient. Very good value for the money. Reviewed on 3 Feb 2026 [](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Berkshire Valley Inn](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/78b361f1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshire Valley Inn 2541 Hancock Rd Williamstown MA - 14 min drive from Fenway Park £103 22 Feb - 23 Feb 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! (566 reviews) Cozy, homey feel of our suite. You can tell the owner takes pride of her inn— cute Pinterest inspiration decoration in the room and lobby. The free breakfast and coffee is a great start to the morning. Close to Jiminy Peak, so easy to ski and come back before the kids fall asleep. Reviewed on 19 Jan 2026 [](https://expedia.co.uk/Williamstown-Hotels-Berkshire-Valley-Inn.h894066.Hotel-Information) ![Jiminy Peak Mountain Resort](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Jiminy Peak Mountain Resort 37 Corey Rd Hancock MA £155 8 Mar - 9 Mar includes taxes & fees Stay at this ski condo in Hancock. Enjoy free parking, 2 restaurants and 2 hot tubs. Our guests praise the property condition in their reviews. Popular attractions ... 8.2/10 Very Good! (989 reviews) This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the ... Reviewed on 5 Oct 2025 [](https://expedia.co.uk/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) [See all 17,767 properties in Massachusetts](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=223) 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. ## More holidays you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holiday packages](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ### Top Ski Holiday Destinations > - [Ski Holidays in Andorra ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/4/Andorra) > - [Ski Holidays in Austria ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/11/Austria) > - [Ski Holidays in Borovets ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/602265/Borovets) > - [Ski Holidays in Bulgaria ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/26/Bulgaria) > - [Ski Holidays in Canada ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/31/Canada) > - [Ski Holidays in Chamonix ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/6050949/Chamonix-Mont-Blanc) > - [Ski Holidays in Finland ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/58/Finland) > - [Ski Holidays in France ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/59/France) > - [Ski Holidays in Italy ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/86/Italy) > - [Ski Holidays in Japan ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/89/Japan) > - [Ski Holidays in Meribel ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/8725/Meribel) > - [Ski Holidays in Norway ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/138/Norway) > - [Ski Holidays in Poland ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/146/Poland) > - [Ski Holidays in Scotland ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/11219/Scotland) > - [Ski Holidays in St-Anton ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/5828/Sankt-Anton-Am-Arlberg) > - [Ski Holidays in Sweden ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/173/Sweden) > - [Ski Holidays in Switzerland ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/174/Switzerland) > - [Ski Holidays in Tignes ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/184273/Tignes) > - [Ski Holidays in Val-D'isere ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/10259/Val-DIsere) ## More Holiday Ideas [Massachusetts Flights ](https://expedia.co.uk/Destinations-In-Massachusetts.d223.Flight-Destinations)[ Massachusetts Hotels ](https://expedia.co.uk/Destinations-In-Massachusetts.d223.Hotel-Destinations)[ Massachusetts Holiday Rentals ](https://expedia.co.uk/Destinations-In-Massachusetts.d223.Holiday-Rental-Destinations)[ Massachusetts Car Hire ](https://expedia.co.uk/Destinations-In-Massachusetts.d223.Car-Hire-Destinations)[ Massachusetts Holidays ](https://expedia.co.uk/Massachusetts.d223.Holidays-City-Breaks)[ Things to do in Massachusetts ](https://expedia.co.uk/Things-To-Do-In-Massachusetts.d223.Travel-Guide-Activities) \* 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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app