Great Barrington Vacations from $571
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Spacious Home in Troy
$571
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
4/10 (1 review)
First of all when we got there we weren't told where the parking area was . We had 5 people staying 3 nights. There were 3 bath mats, 3 bath towels & 2 washcloths. No hand towels. No kitchen towels. The shower head didn't work correctly. Dining area lights didn't work. Control panel on the washer/dryer was falling off. No place to put our clothes. The one dresser had stuff stored in it Master bed sheets had a cigerette burn. Half empty bottles of water laying around. But the worst part was when I did the dishes, all the water from the sink poured into the cupboard and flooded the floor. I cleaned it up & we looked to see if something needed tightening but it was more than that & when I messaged the host was told they would look at it. Nobody came.
Reviewed on May 25, 2026
The Cornell Inn, Lenox & The Berkshires
$859
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.2/10 Wonderful! (1,002 reviews)
We booked a queen room. When we arrived, we were told the AC in our room had stopped working and were given a fan. We were shown to a room with a king bed and later found out our room had been given to another guest who had booked the king room because of the broken AC. We had a terrible nights sleep. We were told a manager would email or call us to refund part of our stay for the inconvenience.
Things that could have been done better.
1) notify guests if there is a problem so they can make other accommodations. We arrived at 6 pm for an 8 pm event and could not make last minute arrangements.
2) Honor guest reservations rather than giving rooms away to preferential guests. No explanation was given for why our room with functioning AC was given away.
3) Make an effort to go buy a window AC or keep one on hand for emergencies.
4) Managers should follow up on poor experiences and refund guests as promised by staff.
Reviewed on Aug 10, 2026
Lodges At Cresthaven
$750
per person
Oct 19 - Oct 23
found 12 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
9.4/10 Exceptional! (621 reviews)
Amazing views of Lake George from our balcony. The kids playground was perfect for our 4 year old and the beach with shallow water area for the kids is perfect. The quick access to the Boat House is just perfect for lunch or dinner. The kayaks and water activities are fun for everyone. We would certainly return!
Reviewed on Aug 9, 2026
Don't see what you're looking for?
See all available trips from Columbus to Great Barrington
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.
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.
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.
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.
Great Barrington Historical Society & Museum
This 1771 Wheeler Farmstead houses a museum with 5,000+ artifacts chronicling Great Barrington's rich past. Explore the historic main house while discovering local heritage through paintings and Native American items.
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.
Three Mile Pond Wildlife Management Area
This serene wildlife refuge offers exceptional birdwatching with over 100 species amid diverse habitats. Explore wheelchair-accessible trails through forests and marshes while spotting native wildlife.
Great Barrington Hotel Deals
Quality Inn Great Barrington
372 Main Street Great Barrington MA
$93 nightly
$103 total
Sep 1 - Sep 2
Total with taxes and fees
The Little Lion
506 Stockbridge Road Great Barrington MA
$125 nightly
$140 total
Sep 1 - Sep 2
Total with taxes and fees
8.6/10 Excellent! (597 reviews)
"Great location. Functional and affordable. Pet friendly."
Reviewed on Aug 6, 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
415 Stockbridge Rd Great Barrington MA
Fully refundable
$123 nightly
$137 total
Sep 9 - Sep 10
Total with taxes and fees
8.8/10 Excellent! (799 reviews)
"Horrible stay. Other guests (young kids) were partying in a adjacent room and running up and down the stairs just outside of my room until 3:30am. Staff at the hotel did little to nothing, so I paid almost $400 to be kept up all night."
Reviewed on Aug 10, 2026
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 |
More vacations you might like
Frequently asked questions
How much does a Great Barrington vacation package cost?
Offering excellent value package deals from $571 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.
Explore a world of travel with Expedia
- Cheap Hotels in Great Barrington
- Hotels with a Pool in Great Barrington
- Stockbridge Hotels
- Hotels near Ski Butternut
- Springfield Hotels
- Hotels near Mahaiwe Performing Arts Center
- Resorts in The Berkshires
- Cottages in Great Barrington
- Resorts & Hotels with Spas in Great Barrington
- Hotels near W.E.B. Du Bois Boyhood Homesite
- Gay friendly Hotels in Great Barrington
- Rv Parks in Stockbridge
- Hotels with Restaurants in Great Barrington
- Historic Hotels in Great Barrington
- Lee Hotels
- Business Hotels in Great Barrington
- Motels in Great Barrington
- Casino Hotels in Great Barrington
- Inns in Great Barrington
- Lenox Hotels
- Extended Stay Hotels in Great Barrington
- Golf Hotels in Great Barrington
- B&B in Great Barrington
- Wyndham Hotels in Great Barrington
- Pet-Friendly Hotels in Great Barrington
- Hotels near Lake Mansfield Park
- Hotels with a Gym in Great Barrington
- Hotels with Bars in Great Barrington
- Great Barrington Hotels
- Pittsfield Hotels
- Hotels with Laundry Facilities in Great Barrington
- Hotels with smoking rooms in Great Barrington
- 5 Star Hotels in Great Barrington
- Boutique Hotels in Great Barrington
- Apartments in Great Barrington
- Hotels on the Lake in Great Barrington
- Hilton Hotels in Great Barrington
- Hotels near Tanglewood Music Center
- Family Hotels in Great Barrington
- Resorts & Hotels with Spas in The Berkshires
- Cabin Rentals in Great Barrington
- Hotels with an Indoor Pool in Great Barrington
- Hotels near Housatonic River Walk
- Cabin Rentals in The Berkshires
- 3 Star Hotels in Great Barrington
- Hotels with Balconies in Great Barrington
- Luxury Hotels in Great Barrington
- Romantic Hotels in Great Barrington
- Hotels with Fireplaces in Great Barrington
- Hotels with Hot Tubs in Great Barrington
- Ski Vacation Packages Great Barrington
- Umpachene Falls Park
- Monterey Vacations
- Ashintully Gardens
- Berkshire Theatre Festival
- Where to stay in Great Barrington
- Mission House
- Bidwell House Museum
- Lee Premium Outlets
- Alford Vacations
- Berkshire Botanical Garden
- Norman Rockwell Museum
- Tanglewood Music Center
- Wyndhurst Golf & Club
- Lee Vacations
- Magnolia Bluffs Casino
- Visit Stockbridge
- Goose Pond Reservation
- Animagic Museum of Animation
- Tyringham Cobble
- Ventfort Hall Mansion and Gilded Age Museum
- Ebenezer II Gifts and Antiques
- Housatonic River Walk
- South Lee Vacations
- Ski Butternut
- National Shrine of the Divine Mercy
- Visit Great Barrington
- Questing
- Visit South Egremont
- Chesterwood
- Stockbridge Vacations
- Naumkeag Museum
- Les Trois Emme Winery
- Berkshire Mountain Country Store
- Budget Rental Cars in Great Barrington
- Avis Rental Cars in Great Barrington
- Addcar rental Rental Cars in Great Barrington
- Car rental Great Barrington
- National Car Rental Rental Cars in Great Barrington
- Alamo Rent A Car Rental Cars in Great Barrington
- Enterprise Rental Cars in Great Barrington
- Hertz Rental Cars in Great Barrington
- Airport Van Rental Rental Cars in Great Barrington
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
