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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is NZ$284 per night from 25 Aug to 26 Aug
NZ$284
25 Aug - 26 Aug
includes taxes & fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
"Very clean. Staff was friendly and responsive."

Reviewed on 6 Aug. 2025

Fairfield Inn & Suites by Marriott Great Barrington Lenox/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 NZ$232 per night from 8 Sept to 9 Sept
NZ$232
8 Sept - 9 Sept
includes taxes & fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
"Amazing service and cheerful staff !!! Thanks so much"

Reviewed on 2 Aug. 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is NZ$174 per night from 4 Sept to 5 Sept
NZ$174
4 Sept - 5 Sept
includes taxes & fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Family trip to the Shrine of Divine Mercy
"The breakfast in the morning was basic & sufficient, clean set up & covered all the bases. The beds were extremely comfortable. I haven’t slept that good in a long time. Maybe I was tired but I definitely slept well."

Reviewed on 5 Aug. 2025

Quality Inn
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