Great Barrington Vacations from $543
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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.
Urban Cowboy Lodge
$880
per person
Dec 3 - Dec 6
found 24 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
9.4/10 Exceptional! (255 reviews)
Food not great for the money loud funk music played at dinner very disappointing paid 52 for a steak all fat breakfast not great we chose to eat elsewhere. The grounds well maintained
Reviewed on Sep 15, 2026
The Old Catskill Game Farm Inn
$2,721
per person
Dec 3 - Dec 6
found 24 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
9.8/10 Exceptional! (35 reviews)
Everything was amazing. Shawn was awesome. He greeted you when we came in. It's definitely experiences. All I can say we had a great time. A little quirky.Amazing history set on 200 acres closed down zoo
Reviewed on Sep 21, 2026
Brook Bound Inn
$658
per person
Oct 29 - Nov 1
found 9 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
9.4/10 Exceptional! (19 reviews)
Our weeklong trip meandering the roads of Vermont was made more memorable by our stay at the Brook Bound Inn! The property is gorgeous and impeccably maintained! Our room was clean and so quiet! The bed was comfortable, and the blackout window blinds allowed us to sleep a little later than normal. The bathroom was very clean with a large shower and great smelling body wash, shampoo, etc. Jake and Hope were so helpful before and during our stay. We also appreciated the robust WIFI. We didn’t try the amazing pool this time, but we will for sure on our next trip!
Reviewed on Aug 30, 2026
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View all tripsStay near popular Great Barrington attractions
Lake Mansfield Park
9.0/10 (22 reviews)
This serene 29-acre lake offers swimming, boating, and fishing amid a conservation forest. Enjoy the sandy beach and shaded picnic areas, or explore wildlife along accessible walking trails through the adjacent woodland.
Photo by Caitlin Reese
Monument Mountain Reservation
You can take time to visit Monument Mountain Reservation during your travels to Great Barrington. While you're here, you can savor the top-notch restaurants.
Ski Butternut
9.0/10 (134 reviews)
Ski Butternut offers 22 diverse trails across 110 acres of terrain suitable for all skill levels. Morning visits reward skiers with freshly groomed slopes and the satisfaction of first tracks.
Mahaiwe Performing Arts Center
9.0/10 (22 reviews)
This 1905 theater offers an intimate setting with exceptional acoustics for music, dance, and film. Enjoy diverse performances in this beautifully restored historic venue known for its perfect sightlines.
Housatonic River Walk
9.2/10 (76 reviews)
Restored from an industrial past, this riverside trail showcases the Housatonic's natural beauty and ecological rebirth. Stroll the free path with interpretive displays highlighting conservation efforts.
Lake Buel
8.8/10 (23 reviews)
This serene Berkshire lake offers clear waters and picturesque surroundings for fishing and boating enthusiasts. Rent a kayak to explore hidden coves or enjoy the spectacular fall foliage reflecting on the water.
Monument Mountain
This historic Berkshire peak inspired Melville and Hawthorne during their famous 1850 hike. Follow their literary footsteps to Devil's Pulpit for panoramic valley views framed by vibrant seasonal foliage.
W.E.B. Du Bois Boyhood Homesite
8.8/10 (29 reviews)
Walk the interpretive trail where civil rights pioneer W.E.B. Du Bois spent his childhood. This National Historic Landmark offers a serene space to reflect on Du Bois's legacy through archaeological remains.
Great Barrington Hotel Deals
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
$101 nightly
$113 total
Oct 18 - Oct 19
Total with taxes and fees
8.6/10 Excellent! (1,010 reviews)
"Good place"
Reviewed on Sep 21, 2026
Prospect Berkshires
50 Prospect Lake Rd Egremont MA
$395 nightly
$441 total
Sep 23 - Sep 24
Total with taxes and fees
The Little Lion
506 Stockbridge Road Great Barrington MA
Fully refundableReserve now, pay when you stay
$115 nightly
$128 total
Oct 18 - Oct 19
Total with taxes and fees
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.
Find the Best Great Barrington Vacation Packages
Great Barrington Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 2,200 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Norman Rockwell Museum, Ski Butternut and Bash Bish Falls State Park |
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:
- Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires: Check in here and take advantage of amenities such as windsurfing and complimentary breakfast.
- Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel: Make happy new memories at this popular retreat which features windsurfing and complimentary breakfast.
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 $543 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.
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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.
