Great Barrington Holiday Packages

Save when you book Great Barrington package deals

Choose two or more items and save on your trip:

Book your Great Barrington holiday

Wotif is here to help you save your hard-earned money.

Combine your flight and hotel bookings into one handy package.

With the extra spending money you can see stacks more in Great Barrington.

Your savings could reach if you lock in a package today. How do you do this? Simply mix and match from more than 550 airlines and 665,000 worldwide properties.

Wotif boasts some of the top prices under the sun. So stop daydreaming and start making new experiences.

Great Barrington Accommodation

Wotif has an excellent range of accommodations in Great Barrington for your upcoming holiday. Reserve your favourite choice today so you can get on with mapping out the rest of your itinerary.

If you can't treat yourself on holidays, when can you? Add some decadence to your well-deserved break by spending your evenings at The Barrington (281 Main St, Level 3). You know you deserve it. If you want something more comfy and easy on the wallet, we've got a couple of excellent options as well. Start with The Briarcliff Motel (506 Stockbridge Road).

Car Hire in Great Barrington

The nearest car rental outlet to Pittsfield Municipal Airport is Enterprise (526 East St), which is a short drive from the airport terminal. You'll have plenty of time to find out a few local secrets from your taxi driver during the ride there.

Holidays to Great Barrington

Isn't it time you gave up fantasising about Great Barrington and got on that plane already? We think it is. But before you start battling with your neighbour for that armrest, let us fill you in on the basics.

Want to picture where you'll be based? Great Barrington is 170 kilometres north of the popular city of New York.

Travelling's about meeting lots of new people and sharing extraordinary experiences. With approximately 2 000 residents in this part of The Berkshires, you're certain to make friends with a few like-minded folk.

Top Great Barrington hotels

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 AU$238 per night from 29 June to 30 June
AU$238
29 June - 30 June
includes taxes & fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG: Business-friendly hotel with free breakfast and free WiFi. Located in the mountains.
"Great place to stay and it is convenient to local theaters and not too far from Tanglewood."

Reviewed on 22 June 2026

Opens in a new windowHoliday Inn Express Hotel & Suites Great Barrington by IHG
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
The price is AU$165 per night from 25 June to 26 June
AU$165
25 June - 26 June
includes taxes & fees
Quality Inn Great Barrington: Business-friendly hotel with free breakfast and free WiFi. Located near ski lifts.
"Room was clean and comfy except for the window A/C unit which quit working about an hour after we turned it on. Opened the windows later at night which helped some, but not a perfect temperature. Did not try the morning continental breakfast because we slept in too late and had to be home by a certain ..."

Reviewed on 22 June 2026

Opens in a new windowQuality Inn Great Barrington
The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road Great Barrington MA
The price is AU$140 per night from 24 June to 25 June
AU$140
24 June - 25 June
includes taxes & fees
The Little Lion: Pet-friendly motel with free WiFi and free parking. Located near ski runs.
"The stay was very good. It was clean and the plumbing worked great. The only issue is the air conditioner was noisy and kept kicking off and on. Other than that, the stay was what one would expect from a top notch motel."

Reviewed on 17 June 2026

Opens in a new windowThe Little Lion
Don't see what you're looking for?
See all available properties in Great Barrington
View all properties
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.

More Destinations