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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

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
The price is AU$186 per night from 6 Apr to 7 Apr
AU$186
per night
6 Apr - 7 Apr
Stay at this business-friendly hotel in North Adams. Enjoy free Wi-Fi, free parking and a 24-hour fitness centre. Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,002 reviews)
For the price, is a good property. Convenient for our purposes. While not up to more modern standards, it is reasonably furnished. Location is a bit noisy due to traffic and trains. Limited decent food options.

Reviewed on 5 Mar 2026

Hotel Downstreet, an Ascend Collection Hotel
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
The price is AU$110 per night from 1 Apr to 2 Apr
AU$110
per night
1 Apr - 2 Apr
Stay at this lodge in Lenox. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in their reviews. ...
9/10 Wonderful! (876 reviews)
I always sleep the best here. So quiet and comfortable. Love the lounge area. Bartender really nice. Had a lovely cheese plate. Shower is great. Great value!

Reviewed on 18 Mar 2026

Berkshires Untold
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
The price is AU$311 per night from 22 Mar to 23 Mar
AU$311
per night
22 Mar - 23 Mar
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! (594 reviews)
one of my favorite places to stay...

Reviewed on 19 Mar 2026

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.

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^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.