Great Barrington Holiday Packages

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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

Prospect Berkshires

Prospect Berkshires

3 out of 5
50 Prospect Lake Rd Egremont MA
The price is AU$537 per night from 8 Jan to 9 Jan
AU$537
8 Jan - 9 Jan 2026
includes taxes & fees
Prospect Berkshires: Pet-friendly hotel with free WiFi and free parking. Located near skiing.
Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession.

Reviewed on 29 Nov 2025

Opens in a new windowProspect 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 AU$178 per night from 4 Jan to 5 Jan
AU$178
4 Jan - 5 Jan 2026
includes taxes & fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG: Business-friendly hotel with free breakfast and free WiFi. Located near skiing.
Very comfortable for a 6 night stay over Thanksgiving while visiting family and friends. One small issue was resolved immediately and was just a communication snafu. Surprisingly good coffee with machines that brew cup by cup. Will return.

Reviewed on 9 Dec 2025

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

Quality Inn

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is AU$126 per night from 6 Jan to 7 Jan
AU$126
6 Jan - 7 Jan 2026
includes taxes & fees
Quality Inn Great Barrington: Business-friendly hotel with free breakfast and free WiFi. Located near skiing.
The rooms were very clean and well kept. The beds were very comfortable. The breakfast: There was no cereal or variety of breads like bagels. Yogurts were great. I do give them the benefit of the doubt on this because it was an off week, in between holidays. It was very quiet. Staff was wonderful. ...

Reviewed on 10 Dec 2025

Opens in a new windowQuality Inn
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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.

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