Great Barrington Holidays
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Top hotels in Great Barrington
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
S$132
1 Sept - 2 Sept
includes taxes & fees
The Little Lion
506 Stockbridge Road Great Barrington MA
Fully refundableReserve now, pay when you stay
S$161
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (597 reviews)
"Great location. Functional and affordable. Pet friendly."
Reviewed on 6 Aug, 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
415 Stockbridge Rd Great Barrington MA
Fully refundable
S$176
9 Sept - 10 Sept
includes taxes & 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 10 Aug, 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)
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 savour 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 theatre 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+ artefacts 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.
Frequently asked questions
How much does a Great Barrington holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday 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'd like to snag a cheap Great Barrington holiday package, consider visiting in March, April and November. You'll generally find better prices on hotels and airfares during these months — ideal for travellers wishing to save money.
How many days is enough for Great Barrington?
Generally, a handful of days is enough to tick off the top attractions during your Great Barrington holiday. But if you prefer to have more time to kick back or go on day trips, think about extending your trip.
Is it worth booking a holiday package to Great Barrington?
It's easy to see why a Great Barrington holiday is on the must-do list of many travellers. Well-known attractions like Housatonic River Walk are just the start of what you can explore here.
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 holiday package well in advance.
Is it cheaper to book a Great Barrington holiday as a package?
You can enjoy significant savings on your Great Barrington escape by booking a personalised holiday package. Check the "Package" heading, then select your travel dates and destination to browse the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday 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.
How to plan a trip to Great Barrington?
- Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Great Barrington.
- Set your budget: Factor in costs such as flights, transportation and food when working out how much to set aside for your trip to Great Barrington. Then, choose a hotel that fits your budget, whether that's a low-cost stay or a lavish getaway.
- Decide how long to go for: Now that you know more about Great Barrington, you can figure out the ideal length of your break. Put together a rough itinerary and give yourself enough time to cover everything you want to do.
- Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a Great Barrington holiday package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
