Great Barrington Vacations

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Find the Best Great Barrington Vacation Packages

Great Barrington Hotel Deals

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 401 per night from Jan 15 to Jan 16
SAR 401
SAR 448 total
15 Jan - 16 Jan
includes taxes & fees
8.8/10 Excellent! (718 reviews)
Nice warm pool and hot tub. Good little fitness center.

Reviewed on 2 January 2026

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Prospect Berkshires

Prospect Berkshires

3 out of 5
50 Prospect Lake Rd Egremont MA
The price is SAR 755 per night from Jan 26 to Jan 27
SAR 755
SAR 969 total
26 Jan - 27 Jan
includes taxes & fees
9.6/10 Exceptional! (18 reviews)
Wonderful stay - the property becomes a beautiful winter wonderland in December! Cabin was warm and well-designed, sauna was amazing and easily accessible all day, the staff was friendly, super responsive and drove us around the property when needed. Would recommend and plan to comeback!

Reviewed on 30 December 2025

Prospect Berkshires
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 413 per night from Jan 14 to Jan 15
SAR 413
SAR 461 total
14 Jan - 15 Jan
includes taxes & fees
8.4/10 Very Good! (547 reviews)
Perfect for pets

Reviewed on 24 December 2025

The Little Lion
See all 1,541 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.

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

Mahaiwe Performing Arts Center

You can enjoy a show at Mahaiwe Performing Arts Center on your trip to Great Barrington. While you're here, you can savor the top-notch restaurants.

Mahaiwe Performing Arts Center

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

Frequently asked questions

How do I find cheap flights to Great Barrington that have flexible change policies?
Search for your affordable airfares to Great Barrington, then click on "No change fee" directly below the "Flexible change policies" heading. It's that easy. We know that travel plans can change and flexibility is important, so book with confidence with Expedia.
Which airlines fly to Great Barrington?
Grab your passport and suitcase and jet away with one of these popular airlines that service Great Barrington:

  • American Airlines - 1,005 flights to or near Great Barrington each month, including 611 flights to Bradley Intl. Airport (BDL) and 394 to Albany Intl. Airport (ALB) per month.
  • United Airlines - 503 flights to or near Great Barrington each month, including 273 flights to Bradley Intl. Airport (BDL) and 229 to Albany Intl. Airport (ALB) per month.

How can I find cheap tickets to Great Barrington?
For an amazing deal to Great Barrington, book well in advance. Also consider using Expedia's "flexible dates" feature above your search results. This will list the cheapest prices for similar time frames. In the last seven days, was the lowest price for a flight to Great Barrington.
How much is a flight to Great Barrington?
If you were journeying one way from (), you could've scored an affordable fare for in the last seven days. Round-trip flights to Great Barrington ranged from only to over the same period.
What are the most popular airports to fly into in Great Barrington?
Which of these two Great Barrington airports you'll fly into will largely depend on your carrier and what you plan to see in the region:

  • Bradley Intl. Airport (BDL) - 1,911 flights per month.
  • Albany Intl. Airport (ALB) - 1,153 flights per month.

When is the cheapest time to fly to Great Barrington?
Departing on a Tuesday, followed by a Monday, is generally the best way to pick up the cheapest airfare. Avoid the weekends if you can, because Saturday is typically the most expensive day. Spend the dollars you saved having a blast in Great Barrington instead!
How much is a plane ticket to Great Barrington?
In the last seven days, airfares to Great Barrington cost between and . Prices depend on the departure time, airline, cabin class and how early the fare is booked.
What months are the cheapest to book a flight to Great Barrington?
To snap up a bargain flight to Great Barrington, book sometime in February when the price of tickets are at their lowest. The most expensive time to book? In the U.S, it's the month of December.
How long is a flight to Great Barrington?
It depends on a couple of things, including where you set off from and whether it's a direct or multi-stop flight. Listed below are three of the most well-known domestic routes to Great Barrington and their average flight times:

  • Orlando, FL (MCO-Orlando Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 48 minutes
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 14 minutes
  • Chicago, IL (ORD-O'Hare Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 12 minutes