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 SAR 252 per night from May 1 to May 2
SAR 252
SAR 281 total
includes taxes & fees
1 May - 2 May
8.2/10 Very Good! (1,002 reviews)
"We like Great Barrington. This is a great location. This is a great value.. We will be back."

Reviewed on 29 March 2025

Quality Inn
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 SAR 465 per night from May 1 to May 2
SAR 465
SAR 520 total
includes taxes & fees
1 May - 2 May
8.8/10 Excellent! (610 reviews)
"Staff was very nice and the room was clean and quiet."

Reviewed on 28 March 2025

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 SAR 287 per night from Apr 30 to May 1
SAR 287
SAR 321 total
includes taxes & fees
30 Apr - 1 May
8.6/10 Excellent! (479 reviews)
"A cozy little inn! I recommend it!"

Reviewed on 9 April 2025

The Little Lion
See all 1,460 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 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.

Discover the most popular places to visit in Great Barrington

Ski Butternut

4.5/5(37 reviews)

Hit the slopes in Great Barrington with a visit to Ski Butternut. While you're in the area, stroll along the lakeside.

Ski Butternut

Housatonic River Walk

4/5(2 reviews)

You can take time to visit Housatonic River Walk during your travels to Great Barrington. Experience the area's theater scene and live music.

Housatonic River Walk

Lake Buel

Commune with nature and explore the great outdoors at Lake Buel during your travels in Great Barrington. While you're here, you can savor the top-notch restaurants.

Lake Buel