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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

Monument Mountain Motel
Monument Mountain Motel
2.5 out of 5
247 Stockbridge Rd, Great Barrington, MA
The price is AU$114 per night from 28 Apr to 29 Apr
AU$114
per night
28 Apr - 29 Apr
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
8.8/10 Excellent! (586 reviews)
"Easy access, very clean, nearby restaurants"

Reviewed on 23 Apr. 2024

Monument Mountain Motel
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$158 per night from 27 Apr to 28 Apr
AU$158
per night
27 Apr - 28 Apr
Stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (572 reviews)
"Lovely indoor pool. Very helpful staff. View of the Berkshires from my window."

Reviewed on 14 Apr. 2024

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
The price is AU$463 per night from 2 May to 3 May
AU$463
per night
2 May - 3 May
Stay at this 4-star hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the clean rooms in our reviews. Popular attractions ...
9.6/10 Exceptional! (292 reviews)
"Perfection. The location is excellent. The Inn is wonderful and everything is done to provide an unforgettable experience to the guests. Highly recommended!"

Reviewed on 4 Apr. 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.