Massachusetts Mountain Vacations and Getaways

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Top Mountain vacation packages in Massachusetts

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Doubletree by Hilton Hotel Leominster
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3 Night Mountain vacations in Massachusetts

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Doubletree by Hilton Hotel Leominster
Don't see what you're looking for?
See all available trips from Columbus to Massachusetts
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4 Night Mountain vacations in Massachusetts

Price found within the past 48 hours. Click for updated prices.
Doubletree by Hilton Hotel Leominster
Don't see what you're looking for?
See all available trips from Columbus to Massachusetts
View all trips

Find amazing mountains vacations in Massachusetts

How to plan for a mountain vacation in Massachusetts?

The first step to planning your mountain vacation to Massachusetts 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 Massachusetts, 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 Massachusetts, from famous chain hotels to charming cabins. The vacation planning page has more tips for organizing your Massachusetts mountain vacation.


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

When booking accommodation for your mountain vacation to Massachusetts, check to see if where you're staying has heating. Massachusetts'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 Massachusetts vacation package.


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

Choosing a package for your Massachusetts 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 Massachusetts package typically include?

Return flight tickets, your accommodation, and applicable taxes are typically included when you book a mountain vacation package to Massachusetts from $769. Hotels may include breakfast and Wi-Fi, while the airfare may include checked luggage. Certain resorts may even include ski passes. As each Massachusetts vacation package is different, be sure to double-check what's included before you confirm. If you want a hassle-free trip, consider booking Massachusetts all-inclusive vacation packages as these include all meals.


How can I book my Massachusetts on Expedia?

Comparing some of the best deals using the search wizard is one of the first steps to booking your Massachusetts 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 Massachusetts 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 Massachusetts 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 Massachusetts 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 Massachusetts 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 Massachusetts 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 Massachusetts vacation packages.


What types of mountain accommodations are available in Massachusetts?

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 Massachusetts. 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 Massachusetts Hotels

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
$140 nightly
The price is $157 total per night from Oct 26 to Oct 27
$157 total
Oct 26 - Oct 27
Total with taxes and fees
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! (982 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 Oct 5, 2025

Jiminy Peak Mountain Resort
Club Wyndham Bentley Brook

Club Wyndham Bentley Brook

3 out of 5
1 Corey Road, Hancock, MA
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! (550 reviews)
quiet and clean

Reviewed on Oct 16, 2025

Club Wyndham Bentley Brook
Cavalier Cottage B&B

Cavalier Cottage B&B

3 out of 5
236 East Oxbow Road, Shelburne Falls, MA
  • 35 min drive from Fenway Park
Stay at this 3-star business-friendly cottage in Shelburne Falls. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Catamount State Forest ...
Would return!
Perfect for a quiet, weekend getaway. We went to celebrate our 5 year anniversary and brought our dog, Ollie. Ollie's a very timid and nervous guy, but he felt very comfortable here. We went during the winter, but would be interested in returning in the summer because there seems to be a lot of outdoor ...

Reviewed on Apr 13, 2018

Cavalier Cottage B&B
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 vacations you might like

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