The Berkshires Mountain Vacations and Getaways

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Photo by Photo courtesy of Berkshire Visitors Bureau
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4 Night Mountain vacations in The Berkshires

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
Club Wyndham Bentley Brook
The Yankee, Trademark Collection by Wyndham
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Find amazing mountains vacations in The Berkshires

How to plan for a mountain vacation in The Berkshires?

The first step to planning your mountain vacation to The Berkshires is to decide what dates you want to go. In the winter months, fresh snowfall means you could hit the slopes at ski resorts near The Berkshires, while summer invites you to enjoy scenic hikes. It's a good idea to choose the type of accommodation you'd prefer, too. On Expedia, you'll encounter a vast array of options in The Berkshires, from famous chain hotels to charming cabins. The vacation planning page has more tips for organizing your The Berkshires mountain vacation.


What amenities should I look for when booking a mountain resort in The Berkshires?

When booking accommodation for your mountain vacation to The Berkshires, check to see if where you're staying has heating. The Berkshires's mountain air means it can feel fresh at night. If you're craving a special stay, look to see if the hotel offers mountain view rooms, or has a pool or hot tub to unwind in the evenings. Expedia's handy search filters include all these amenities and more, making it a breeze to book the right place to stay on your The Berkshires vacation package.


Why should I choose a package for my mountain vacation in The Berkshires?

Choosing a package for your The Berkshires vacation often works out cheaper thanks to the savings you get for bundling up your flights and hotel. You'll typically find it costs more when booking these separately. On Expedia, the green label even shows you how much you're saving. Packages also tend to be more flexible, meaning it's more likely you can cancel for free in case your 2025 plans change. You can usually secure your package by paying a small upfront deposit, whereas booking flights separately requires full payment.


What does a The Berkshires package typically include?

Return flight tickets, your accommodation, and applicable taxes are typically included when you book a mountain vacation package to The Berkshires from $381. Hotels may include breakfast and Wi-Fi, while the airfare may include checked luggage. Certain resorts may even include ski passes. As each The Berkshires vacation package is different, be sure to double-check what's included before you confirm. If you want a hassle-free trip, consider booking The Berkshires all-inclusive vacation packages as these include all meals.


How can I book my The Berkshires on Expedia?

Comparing some of the best deals using the search wizard is one of the first steps to booking your The Berkshires mountain vacation on Expedia. Take advantage of the search filters to narrow down hundreds of options at the click of a button. If you've got a strict budget, use the maximum price filter to set your limit. When you've pinned down your The Berkshires package vacation, book it in just a few clicks. You'll also have the option to spread the cost with Expedia's payment plans.


Why book your The Berkshires mountain vacation with Expedia?

With meaty exclusive deals you won't find anywhere else, you'll keep more cash in your pocket when booking your The Berkshires vacation package on Expedia. No matter your preferences or tastes, you'll find the right place to stay thanks to the wide selection of accommodation. There are even last-minute deals, too. And if that's not enough, join One Key for free. Expedia's reward program lets you earn points on eligible trips and also gives you access to juicy member-only discounts.


Can I cancel my mountain vacation package booking?

Yes, as most of Expedia's mountain vacation packages to The Berkshires are flexible, you can often cancel for free. Doing so is easy, too—log in to the “Trips” section and follow the steps. Don't forget to double-check the cancellation policy before booking, as not all The Berkshires vacation packages are flexible. The good news is Expedia will display this to you before payment. Take advantage of the free cancellation search filter so you'll be able to narrow down your search to view only flexible The Berkshires vacation packages.


What types of mountain accommodations are available in The Berkshires?

5-star hotels, cozy mountain lodges, and quaint bed and breakfasts are some of the most popular types of mountain accommodations for your vacation to The Berkshires. Don't forget to use the filters to home in the amenities you'd like to have, too. Maybe it's a spacious suite with a mountain view or a traditional lobby with a fireplace—you'll find it all with Expedia's easy-to-use search wizard and wide choice of accommodation.

Top Mountain The Berkshires Hotels

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
  • 34 min drive from Tanglewood Music Center
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 hot tubs. Our guests praise the property condition in our reviews. Popular ...
8.2/10 Very Good! (962 reviews)
Good base to do things in the Berkshires
"We didn't spend much time there, but it was nice, comfortable, clean and quiet. It was close to the things we had planned to do."

Reviewed on Aug 11, 2025

Jiminy Peak Mountain Resort
Club Wyndham Bentley Brook

Club Wyndham Bentley Brook

3 out of 5
1 Corey Road, Hancock, MA
  • 34 min drive from Tanglewood Music Center
Stay at this 3-star ski hotel in Hancock. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition ...
9.2/10 Wonderful! (533 reviews)
"Loved all of the jacuzzis as well as the apartment condo style sleeping. So convenient for access to Jiminy Peak for summer fun and I'm sure it great for skiers."

Reviewed on Aug 7, 2025

Club Wyndham Bentley Brook
Chambery Inn

Chambery Inn

3 out of 5
199 Main St, Lee, MA
  • 8 min drive from Tanglewood Music Center
Stay at this 3-star B&B in Lee. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Tanglewood Music Center and Berkshire Mountain ...
9.4/10 Exceptional! (368 reviews)
"Beautiful stay. We booked last minute and it was amazing! We were able to book the room with jacuzzi and a fireplace—which made the whole stay so romantic. Will recommend and am planning to visit regularly. Hoping to return in the fall but definitely next spring. This family works hard and takes ..."

Reviewed on Jun 13, 2025

Chambery 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.

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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.