Great Barrington Trips (flight + hotel)

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to P 3,118 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Great Barrington

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 P5,290 per night from Sep 2 to Sep 3
P5,290
P5,909 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"Good"

Reviewed on Aug 8, 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
Fully refundableReserve now, pay when you stay
The price is P8,621 per night from Aug 25 to Aug 26
P8,621
P9,630 total
Aug 25 - Aug 26
includes taxes & fees
9.2/10 Wonderful! (724 reviews)
"Very clean. Staff was friendly and responsive."

Reviewed on Aug 6, 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 P7,080 per night from Sep 1 to Sep 2
P7,080
P7,908 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 1,539 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.

Popular places to visit

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.

Great Barrington Historical Society & Museum

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.