Great Barrington Vacations

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Find the Best Great Barrington Vacation Packages

Great Barrington Hotel Deals

Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is ₩128,391 per night from Sep 2 to Sep 3
₩128,391
₩143,413 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"Close to city center, safe and great costumer experience"

Reviewed on Jul 30, 2025

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
The price is ₩209,250 per night from Aug 25 to Aug 26
₩209,250
₩233,732 total
Aug 25 - Aug 26
includes taxes & fees
9.2/10 Wonderful! (723 reviews)
"Was the perfect stop over for our way home. All the employees were extremely friendly."

Reviewed on Aug 1, 2025

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA
Fully refundable
The price is ₩171,834 per night from Sep 1 to Sep 2
₩171,834
₩191,939 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (643 reviews)
"Amazing service and cheerful staff !!! Thanks so much"

Reviewed on Aug 2, 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
See all 1,536 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.

Frequently asked questions

How much does a Great Barrington vacation package cost?
Offering excellent value package deals 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'd like to snag a cheap Great Barrington vacation package, consider visiting in March, April and November. You'll generally find better prices on hotels and airfares during these months — ideal for travelers 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 vacation. 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 vacation package to Great Barrington?
It's easy to see why a Great Barrington vacation is on the must-do list of many travelers. 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 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.
How to plan a trip to Great Barrington?

  1. Pick the best time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to go to Great Barrington.
  2. 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.
  3. 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.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a Great Barrington vacation 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.