The Berkshires Ski Holidays

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Photo by Photo courtesy of Berkshire Visitors Bureau
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How to find The Berkshires ski packages?

What kind of ski holiday packages are available in The Berkshires?

Expedia offers a wide variety of ski holiday packages. To find out what packages are currently available, just search Expedia for The Berkshires ski packages 2025 and start planning your next ski trip.

How can I book a ski holiday in The Berkshires with Expedia?

Go to the search bar and select “Packages”. Then, choose your destination and the dates of your stay, and browse the list of The Berkshires ski packages to find your perfect ski holiday.

Are ski holidays in The Berkshires suitable for families?

The Berkshires ski holidays can be a great option for families. You can enrol your children in skiing lessons if they’re beginners or spend the days on the slopes with them if they’re already experienced skiers. If your children are too young to ski themselves, look for family-friendly accommodation that offers childcare services and activities for non-skiing family members.

What’s the best way to plan a skiing holiday in in The Berkshires?

Planning a ski holiday to The Berkshires couldn’t be simpler. Just choose your destination and when you want to go, and Expedia will take care of the rest. Once you’ve selected where and when you want to go, Expedia will provide you with several ski packages for that time and place for you to choose from.

What are some tips for choosing a ski package in in The Berkshires?

Before searching for ski packages to The Berkshires, define your priorities. Are you looking for a family-friendly resort, luxury accommodations, budget-friendly options, or specific ski terrain? Knowing your preferences will help you narrow down your choices.

How can I find excellent deals on ski holidays in in The Berkshires?

One of the most reliable ways to get a good deal for 2025 is to book your The Berkshires ski holiday well in advance. Resorts often offer early booking discounts, and you’ll have a wider selection of accommodations to choose from.

How can I grab last-minute ski holiday deals in The Berkshires?

Just enter your dates and see what’s available. This way you might be able to nab some great last-minute The Berkshires ski packages.

Are pet-friendly ski holiday packages available in The Berkshires?

To find pet-friendly The Berkshires ski packages in 2025, once you’ve entered your dates, use the filters on the left and select “Pet-friendly” under “Amenities” and the pet-friendly ski resort packages will show up.

How can I find great weekend ski holiday packages in The Berkshires?

Enter your weekend dates and search Expedia’s The Berkshires ski trip packages to find the ones that are available for the weekend of your choice. You can sort by price to find The Berkshires ski holidays that suit your wallet.

How can I find the cheapest ski holidays in in The Berkshires?

Once you’ve entered your travel dates, use the sort by filter at the top right to sort by price and find The Berkshires ski holidays that won’t break the bank. Plus, booking well in advance can help you find cheaper rates. Be sure to check out Expedia’s The Berkshires ski packages including flights as you could save money by booking everything together.

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

Expedia lets you bundle up your stay, flight, and car rental for some cool discounts on The Berkshires ski packages that will have you carving through the powder without burning a hole in your pocket.

Can I cancel my ski holiday booking in The Berkshires with Expedia?

Yes, numerous The Berkshires ski packages offer free cancellation, giving you the freedom to put the brakes on your trip in the event of unforeseen circumstances.

Top Ski The Berkshires Hotels

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
  • 35 min drive from Tanglewood Music Center
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,912 reviews)
"My husband and I stayed here for the last section of our vacation. The property was excellent-very clean & very quiet. Only thing was all parking was on gravel and on an angle so hard to find a safe spot for our motorcycle."

Reviewed on 29 Jul. 2025

Vacation Village in the Berkshires
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
  • 8 min drive from Tanglewood Music Center
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,000 reviews)
"Everything fine except breakfast. Under construction"

Reviewed on 30 Jul. 2025

The Yankee, Trademark Collection by Wyndham
Berkshire Valley Inn

Berkshire Valley Inn

2.5 out of 5
2541 Hancock Rd, Williamstown, MA
  • 42 min drive from Tanglewood Music Center
Stay at this hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (553 reviews)
"Would have liked daily maid service. Would have liked breakfast to be extended to 9:30."

Reviewed on 13 Jul. 2025

Berkshire Valley Inn
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.