Great Barrington Vacation Packages
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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!
Top Great Barrington Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Albany Airport
CA $1,687
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
8.6/10 Excellent! (1,842 reviews)
Th room
Was filthy. Lamp shades were dirty
Carpet felt like food and dirt in it
The blinds had holes in it little bigger than a pin hole
Enough to get light in room to annoy you
Homeless people living there and hanging outside drinking
Horrible experience
Reviewed on Sep 15, 2026
Ready to book your vacation to Great Barrington?
Great Barrington Hotel Deals
Quality Inn Great Barrington
372 Main Street Great Barrington MA
CA $144
CA $160 total
Sep 21 - Sep 22
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"Beds were comfortable but the pillows not so great but clean and quiet."
Reviewed on Sep 15, 2026
Prospect Berkshires
50 Prospect Lake Rd Egremont MA
CA $449
CA $548 total
Sep 16 - Sep 17
includes taxes & fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
415 Stockbridge Rd Great Barrington MA
Fully refundable
CA $179
CA $200 total
Sep 20 - Sep 21
includes taxes & fees
8.8/10 Excellent! (823 reviews)
"The location is very convenient. We have been going and staying at this hotel for the past 6 years every time we come to the Berkshire area."
Reviewed on Sep 13, 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.
Stay near popular Great Barrington attractions
Lake Mansfield Park
9.0/10 (22 reviews)
Explore the great outdoors at Lake Mansfield Park, a lovely green space in Great Barrington. Experience the area's theater scene and live music.
Ski Butternut
9.0/10 (134 reviews)
Hit the slopes in Great Barrington with a visit to Ski Butternut. While you're in the area, stroll along the lakeside.
Mahaiwe Performing Arts Center
9.0/10 (22 reviews)
Enjoy a stop at Mahaiwe Performing Arts Center, an entertaining place to visit in Great Barrington. While you're here, you can savor the top-notch restaurants.
Housatonic River Walk
9.2/10 (76 reviews)
You can take time to visit Housatonic River Walk during your travels to Great Barrington. Experience the area's theater scene and live music.
Lake Buel
8.8/10 (23 reviews)
Commune with nature and explore the great outdoors at Lake Buel during your travels in Great Barrington. While you're here, you can savor the top-notch restaurants.
Monument Mountain
Learn about the local history of Great Barrington with a stop at Monument Mountain. While you're here, you can savor the top-notch restaurants.
W.E.B. Du Bois Boyhood Homesite
8.8/10 (29 reviews)
You can learn about the history of Great Barrington with a visit to W.E.B. Du Bois Boyhood Homesite. While you're in the area, stroll along the lakeside.
Great Barrington Historical Society & Museum
You can spend time studying the exhibits at Great Barrington Historical Society & Museum during your trip to Great Barrington. While you're here, you can savor the top-notch restaurants.
Frequently asked questions
How much does a Great Barrington vacation package cost?
Offering excellent value package deals from CA $1,553 on Expedia, you'll be pleasantly surprised at how much a vacation to Great Barrington costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Great Barrington?
You can typically find lower rates and greater availability in March, April and November. Explore our cheap Great Barrington vacation packages and you could land some great off-season discounts.
How many days is enough for Great Barrington?
With a well-planned itinerary, you can easily tick off the most popular Great Barrington sights in a few days. But if you want to venture off the beaten track or go on day tours, consider booking your Great Barrington vacation for longer.
Is it worth booking a vacation package to Great Barrington?
Great Barrington offers everything you need for an amazing trip. Begin your Great Barrington vacation on a high note by exploring popular attractions like Housatonic River Walk.
How to find the best Great Barrington package deals?
Start your search for a Great Barrington package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Great Barrington package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Great Barrington escape underway.
Is it cheaper to book a Great Barrington vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Great Barrington vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Great Barrington?
If you've got your Great Barrington travel dates locked in, book early to bag some incredible deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Great Barrington?
- Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Great Barrington.
- Plan your budget wisely: Besides the price of your hotel, you'll need to factor in other expenses. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that may arise during your trip to Great Barrington.
- Work out your trip length: Think about how long you want to spend exploring Great Barrington. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
- Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a customized Great Barrington vacation package.
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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.
