Great Barrington Vacations from ￥243,070

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The Latest Great Barrington Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
per person
Oct 10 - Oct 14
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Albany (ALB)
8.6/10 Excellent! (1,014 reviews)
Prixw reasonable with good service

Reviewed on Jul 31, 2025

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
per person
Oct 10 - Oct 14
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Albany (ALB)
8.6/10 Excellent! (1,931 reviews)
The room was far bigger than we expected. Great location - staff at the welcome desk were super friendly and helpful.

Reviewed on Aug 7, 2025

Hilton Garden Inn Saratoga Springs

Hilton Garden Inn Saratoga Springs

3 out of 5
per person
Oct 10 - Oct 14
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Albany (ALB)
8.2/10 Very Good! (1,003 reviews)
The property is located in a perfect spot. Very close to town, close to Racetrack and Casino. The place could definitely use some updating. I only stayed one night and I would stay there again bc if the lication

Reviewed on Aug 4, 2025

La Quinta Inn & Suites by Wyndham Latham Albany Airport

La Quinta Inn & Suites by Wyndham Latham Albany Airport

3 out of 5
per person
Oct 10 - Oct 14
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Albany (ALB)
7.4/10 Good! (1,001 reviews)
No hot water in the sinks, rust in tub area, keys didn’t work properly

Reviewed on Aug 4, 2025

Holiday Inn Express and Suites Albany Airport- Wolf Road by IHG

Holiday Inn Express and Suites Albany Airport- Wolf Road by IHG

2.5 out of 5
per person
Oct 10 - Oct 14
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Albany (ALB)
8.6/10 Excellent! (1,032 reviews)
Great stay and very clean

Reviewed on Aug 2, 2025

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 ￥13,640 per night from Sep 2 to Sep 3
￥13,640
￥15,237 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Nice motel in the city center"

Reviewed on Aug 6, 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 ￥22,230 per night from Aug 25 to Aug 26
￥22,230
￥24,831 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 ￥18,255 per night from Sep 1 to Sep 2
￥18,255
￥20,390 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 from ￥243,070 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.