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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
American Airlines
American Airlines
United
United
American Airlines
American Airlines
United
American Airlines
American Airlines

Flight Info
Destination airport
Bradley Intl.
Destination city name
Hartford
Return price
AU$578

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$324 per night from 16 Mar to 17 Mar
AU$324
includes taxes & fees
16 Mar - 17 Mar
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! (419 reviews)
Cozy New England Inn
"This was my first stay at the Williams Inn and I found it the coziest hotel I've stayed at! The furnishings are lovely and the lobby area very inviting (especially in the winter when the fire is always going). There's also - unfortunately, I didn't discover this until the end of my stay - a little ..."

Reviewed on 25 Feb. 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$184 per night from 21 Mar to 22 Mar
AU$184
includes taxes & fees
21 Mar - 22 Mar
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! (750 reviews)
Very good experience
"Arrived late and restaurant staff were very helpful preparing me a late night take out meal. Breakfast very good. Allowed me to check out late as I was waiting for a ride."

Reviewed on 12 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 26 Mar to 27 Mar
AU$119
includes taxes & fees
26 Mar - 27 Mar
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! (1,001 reviews)
"Facilities maintained well, although the tub in my room needs to be replaced and freezer in mini-fridge didn’t adequately chill the ice block for my cooler. Everything clean and neat. Snow and ice removed from sidewalks and parking lot. Friendly and helpful staff in the evening (middle of a rainstorm) ..."

Reviewed on 11 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.