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

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$295 per night from 1 July to 2 July
NZ$295
1 July - 2 July
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 ...
"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
Fully refundable
The price is NZ$234 per night from 19 July to 20 July
NZ$234
19 July - 20 July
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 ...
"Well-located just off main street and a block from restaurants and shops. Rooms were spacious and clean. Reception staff were helpful. Breakfast a good way to start the day with decent choices. Reasonably priced, given the area."

Reviewed on 26 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
Fully refundableReserve now, pay when you stay
The price is NZ$237 per night from 8 July to 9 July
NZ$237
8 July - 9 July
includes taxes & fees
Stay at this motel in Great Barrington. Enjoy free Wi-Fi, free parking and a garden. Our guests praise the helpful staff in their reviews. Popular attractions ...
"Really nice, peaceful, clean, very comfortable mattress. Convenient check - in! I will be a repeat customer"

Reviewed on 26 June 2026

Opens in a new windowThe Little Lion
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