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 accommodation 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

Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is NZ$128 per night from 14 May to 15 May
NZ$128
14 May - 15 May
includes taxes & fees
Stay at this motel in Great Barrington. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the helpful staff and the clean rooms in their ...
Good

Reviewed on 11 May 2026

Opens in a new windowMonument Mountain Motel
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 NZ$232 per night from 27 May to 28 May
NZ$232
27 May - 28 May
includes taxes & fees
Stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean ...
Quick check in. Nice room!

Reviewed on 10 May 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
Fully refundable
The price is NZ$159 per night from 17 May to 18 May
NZ$159
17 May - 18 May
includes taxes & fees
Stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
really enjoyed my stay here. The staff are friendly and helpful, the rooms are very clean and well put together, the bed was comfortable, and conveniently, there's a CVS right in the hotel parking lot, which is great if you, like me, forgot to pack something or needed something more than what the ...

Reviewed on 11 May 2026

Opens in a new windowQuality Inn Great Barrington
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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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