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How Much Does it Cost To Fly To The Berkshires?

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

United
United
United
American Airlines
United
United
United
Qantas Airways
American Airlines
Qantas Airways

Flight Info
Destination airport
Bradley Intl.
Destination city name
Hartford
Return price
AU$2,518

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

The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
The price is AU$397 per night from 1 Apr to 2 Apr
AU$397
includes taxes & fees
1 Apr - 2 Apr
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! (430 reviews)
"Wonderful!"

Reviewed on 26 Mar. 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$185 per night from 12 Apr to 13 Apr
AU$185
includes taxes & fees
12 Apr - 13 Apr
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! (763 reviews)
"Easy check in, nice staff. Rug in the room was kind of musty. They were accommodating to me requesting to have a slightly later check out. Would return if in the area."

Reviewed on 18 Mar. 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Quality Inn
Quality Inn
2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is AU$119 per night from 13 Apr to 14 Apr
AU$119
includes taxes & fees
13 Apr - 14 Apr
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 ...
8.2/10 Very Good! (1,005 reviews)
"We like Great Barrington. This is a great location. This is a great value.. We will be back."

Reviewed on 29 Mar. 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.

^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.