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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!

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Hotels in The Berkshires

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3 out of 5
One West Street, Pittsfield, MA
The price is AU$177 per night from 5 Jan to 6 Jan
AU$177
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (701 reviews)
"Staff was very accommodating. The pool area was quite nice and it was deep"

Reviewed on 16 Dec. 2024

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Quality Inn
Quality Inn
2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is AU$151 per night from 29 Dec to 30 Dec
AU$151
includes taxes & fees
29 Dec - 30 Dec
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 ...
8/10 Very Good! (1,000 reviews)
"Friendly staff"

Reviewed on 16 Dec. 2024

Quality Inn
The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
The price is AU$336 per night from 1 Jan to 2 Jan
AU$336
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (389 reviews)
"It was a very positive experience. I would return."

Reviewed on 16 Dec. 2024

The Williams 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.

^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.