Great Barrington Vacations from $316

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Your Great Barrington Vacation

Say goodbye to the worries of planning and hello to a Great Barrington vacation package. With the finer details organized before you take off, you can focus on discovering the best of this city, starting with Canann Village Historic District, which is good for dining, culture and shopping. Fill your spare time with visits to Ski Butternut, Housatonic River Walk and Lake Buel, some of the things you simply have to see during a trip to Great Barrington. Expedia is here to help you escape the everyday. Tailor your vacation to Great Barrington to suit your travel style, whatever that may be!

The Latest Great Barrington vacation packages

Price found within the past 48 hours. Click for updated prices.
Ambler Hotel
The Perch Hotel
Lodges At Cresthaven
Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views
Hilton Garden Inn Saratoga Springs
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Great Barrington Hotel Deals

Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
$93 nightly
The price is $104 total per night from Sep 1 to Sep 2
$104 total
Sep 1 - Sep 2
Total includes taxes and fees
8.2/10 Very Good! (1,005 reviews)
"Good"

Reviewed on Aug 8, 2025

Quality Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $187 total per night from Aug 25 to Aug 26
$187 total
Aug 25 - Aug 26
Total includes taxes and fees
9.2/10 Wonderful! (724 reviews)
"Very clean. Staff was friendly and responsive."

Reviewed on Aug 6, 2025

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA
Fully refundable
$124 nightly
The price is $139 total per night from Sep 1 to Sep 2
$139 total
Sep 1 - Sep 2
Total includes taxes and fees
8.8/10 Excellent! (647 reviews)
"It was overpriced"

Reviewed on Aug 10, 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
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.

Great Barrington Ski Vacation Packages

Do it your way with one of our Great Barrington ski vacation packages. Whether you're after an adrenaline-filled adventure, some respite at altitude or a bit of both, your ultimate getaway begins with Expedia. Travel to Great Barrington between December and March and choose from about 22 runs operating at this renowned ski spot in United States of America. Make your way to a beginners' area and hone your skills before going downhill skiing. If you need some extra gear, you can rent it at the ski village. When it's time to hang up your skis, head on over to the resort's day spa. It's the perfect way to recharge your batteries following hours of endless fun. A family ski vacation in Great Barrington is a wonderful opportunity to enjoy new things with your gang. Once you've all honed your skiing technique, be sure to go snowboarding and tobogganing.

How To Get Around

Pick up one of Expedia's Great Barrington vacation packages and your next unforgettable adventure is just a flight away. After landing at Albany International Airport, it's one hour to reach this terrific ski destination. It takes 10 minutes to arrive at the runs from the middle of Great Barrington, and parking is free. If you're driving during winter, tire chains are recommended. Save big bucks on your ski vacation when you bundle your bookings. Select from a season-pass ticket or a full-day ticket, then combine your hotel, flights and a car rental into a package to get the cheapest price possible. Scroll through our Great Barrington ski package deals for some ideas.

Great Barrington Ski Accommodations

Expedia also has your back if you'd prefer a vacation package that includes a hotel. You'll find 2 lodging options in and around Great Barrington where you can rest up after an energetic day on the snow. Here are our best picks:

For even more inspiration, browse Expedia's entire selection of Great Barrington accommodations and start planning your ski vacation!

Great Barrington Resort Ski Info

Average yearly snowfall
10 ft
Elevation of lowest ski lift
820 ft
Cost of 1-day lift pass
Under $75
Easy runs
8
Moderate runs
8
Advanced runs
6
Longest run
1.5 mi

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Frequently asked questions

How much does a Great Barrington vacation package cost?
Offering excellent value package deals from $316 on Expedia, you'll be thrilled with how little a vacation to Great Barrington costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Great Barrington?
If you're looking to book a cheap Great Barrington vacation package, consider planning a trip in October, November and December. You'll generally find lower rates on flights and hotels during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Great Barrington?
With a well-organized schedule, you can easily visit the top Great Barrington sights in a handful of days. But if you'd like to discover lesser-known spots or go on day trips, consider booking your Great Barrington vacation for longer.
Is it worth booking a vacation package to Great Barrington?
Great Barrington is a good vacation destination with attractions like Ski Butternut among the many things to keep you entertained. Whether you're traveling with the family or getting away with friends, a Great Barrington vacation promises a good time for everyone.
How to find the best Great Barrington package deals?
Use Expedia's handy filters to find some unbeatable Great Barrington package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Great Barrington package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Great Barrington vacation as a package?
You can enjoy significant savings on your Great Barrington escape by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Great Barrington?
If you've got your Great Barrington travel dates confirmed, book as early as you can to score some outstanding deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later Great Barrington vacation packages?
If you're like us, you love going away but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Great Barrington trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.