Great Barrington Packages (Flight + Hotel)

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Top hotels in Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundable
The price is ฿3,751 per night from 2 Aug to 3 Aug
฿3,751
฿4,189 total
2 Aug - 3 Aug
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"The hotel reminded me of traveling in the 1960’s and 70’s staying at motels. Plastic chairs sitting outside each room on the concrete. Carpeting in the room always leaves me wondering how clean it is. Bathroom was clean but towels are very lightweight. Train track right behind the parking lot and ..."

Reviewed on 4 Jul 2026

Quality Inn Great Barrington
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 ฿5,474 per night from 27 Jul to 28 Jul
฿5,474
฿6,115 total
27 Jul - 28 Jul
includes taxes & fees
8.8/10 Excellent! (783 reviews)
"Clea room and amenities"

Reviewed on 4 Jul 2026

Holiday Inn Express Hotel & Suites Great Barrington by IHG
The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is ฿3,716 per night from 7 Jul to 8 Jul
฿3,716
฿4,150 total
7 Jul - 8 Jul
includes taxes & fees
8.6/10 Excellent! (576 reviews)
"Super comfortable. Clean, not fussy, easy check-in/check out. Close to Tanglewood ! Breakfast at nearby Red Lion with a cup of coffee on the porch was excellent!"

Reviewed on 4 Jul 2026

The Little Lion
See all 1,592 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

A lake surrounded by autumn-colored trees.

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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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?

  1. 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.
  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 holiday package that brings all your bookings together.

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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.