Great Barrington Vacations

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Find the Best Great Barrington Vacation Packages

Great Barrington Hotel Deals

Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
AED 280
AED 313 total
1 Nov - 2 Nov
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."

Reviewed on 5 October 2026

Quality Inn Great Barrington
Prospect Berkshires

Prospect Berkshires

50 Prospect Lake Rd Egremont MA
AED 1,140
AED 1,397 total
2 Nov - 3 Nov
includes taxes & fees
10/10 Exceptional! (45 reviews)
"Absolutely spectacular resort! Could not have enjoyed more."

Reviewed on 4 October 2026

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

249 Stockbridge Rd Great Barrington MA
AED 528
AED 589 total
2 Nov - 3 Nov
includes taxes & fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
See all 1,597 properties in Great Barrington
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)
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.
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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.
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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.
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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.
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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.
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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.
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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.
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Jug End State Reservation

8.8/10 (3 reviews)
This Berkshire Mountains sanctuary offers a 2-mile loop through meadows and forests with panoramic valley views. Autumn visitors are rewarded with vibrant foliage displays along well-maintained, uncrowded trails.
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Frequently asked questions

How much does a Great Barrington vacation package cost?
Offering excellent value package deals 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 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?
  1. 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.
  2. 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.
  3. 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.
  4. 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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