Search The Berkshires Flights

Change your flight without a fee on select flights

Money Saving Bundle when you purchase Hotel + Flight! 

Get mobile alerts about flight delays, gate changes and more with the FREE Wotif app


Flight Info
Destination airport
The Berkshires

Flights To The Berkshires

Once you’ve decided where to go on your next holiday, the fun part begins! Wotif makes it easy (and yes, even fun!) to compare flights to The Berkshires, so you can get the best deals and save that dough for exploring your new favourite place. Speaking of exploring, it’s time to start planning your itinerary. Whether you love off-the-beaten-path neighbourhoods or busy shopping and dining districts, you’re sure to find what you’re looking for. Hit up top-rated restaurants and hidden local haunts, snap some photos of historic landmarks and make a few friends along the way—starting with your aisle mate on the plane.

No matter where you call home, we’ve got The Berkshires flights that will get you from point A to point B in style and comfort. Ready to start packing? It’s OK to be “that passenger” in your matching tracksuit and eye mask, snoozing right up until the final descent. After all, nothing says “holiday” more than a good nap! If you don’t want to surrender a second of your trip to sleep, grab a cup of coffee and chat with fellow travellers or plug in to a flick that takes place in your destination city—it’s like cultural anthropology. For science!

OK, traveller. Let’s do this. Sweet plans? Tick. Craving for adventure? You got it. Entertainment for the flight? Packed. Cheap flights to The Berkshires? Book them with Wotif for great deals on travel that fits your schedule and airlines that fit your price range. And last but not least, unforgettable holiday memories? They’re already in the works!

Need a Car For After Your Flight?

Hotels in The Berkshires

The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
The price is AU$318 per night from 23 Dec to 24 Dec
AU$318
per night
23 Dec - 24 Dec
Stay at this business-friendly hotel in Williamstown. Enjoy free Wi-Fi, free parking and a fitness centre. Our guests praise the helpful staff in their reviews. ...
9.6/10 Exceptional! (549 reviews)
Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick.

Reviewed on 7 Dec 2025

The Williams Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
The price is AU$156 per night from 17 Dec to 18 Dec
AU$156
per night
17 Dec - 18 Dec
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8/10 Very Good! (986 reviews)
Clean and comfortable

Reviewed on 7 Dec 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street Great Barrington MA
The price is AU$127 per night from 28 Dec to 29 Dec
AU$127
per night
28 Dec - 29 Dec
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 ...
8.4/10 Very Good! (1,002 reviews)
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

Quality Inn
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

^Savings based on all package bookings made with Flight + Hotel on Wotif.com from , as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.