Sheffield Holiday Packages

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Wotif has some of the most competitive deals under the sun. Better find your passport — right now is the time to take to the skies.

Sheffield Accommodation

With only 3 accommodations in Sheffield, securing a place to stay should be at the very top of your to-do list. Wotif has some top deals on offer right now, so what are you waiting for?

Whether you're planning to spend a lot of time under the soft covers or you think you might be cruising around town for most of your holiday, The Windflower Inn and The Egremont Village Inn are highly recommended accommodation options.

Car Hire in Sheffield

If you're headed to Pittsfield Municipal Airport, you'll have to venture futher afield to hire a set of wheels. The closest outlet is Enterprise (526 East St), which is a short drive from the terminal.

Holidays to Sheffield

Sheffield is calling you — are you ready to answer it? It's time to experience this spectacular destination for yourself. But before you hightail it out the door, here are the essentials.

Sheffield is surrounded by a couple of major cities that should help you get your bearings. Just 35 kilometres to the northwest is Hudson. The town isn't too far from Torrington either. You only need to travel southeast for 40 kilometres before you hit it.

Some 3 000 people call this part of The Berkshires home. So, if you're hoping to meet some new buddies, you won't have too many problems.

Top Sheffield hotels

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street Sheffield MA
Fully refundableReserve now, pay when you stay
The price is AU$266 per night from 20 May to 21 May
AU$266
20 May - 21 May
includes taxes & fees
Wilder House Berkshires: Bed & breakfast with free breakfast and free WiFi.
Very comfortable bed, that was mostly what I cared about. I got my beauty sleep)

Reviewed on 11 May 2026

Opens in a new windowWilder House Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is AU$167 per night from 24 May to 25 May
AU$167
24 May - 25 May
includes taxes & fees
Berkshire Mountain Lodge: Business-friendly lodge with free WiFi and free parking. Located next to a golf course.
Loved this place - and would probably come. again. My only issue is that check-out is at 10:00 am. I had friends staying there who were not checking out, so I was able to linger in their suite. I imagine that I could have eaten breakfast in the large sunny open lounge on the first floor - if this ...

Reviewed on 14 May 2026

Opens in a new windowBerkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is AU$166 per night from 21 May to 22 May
AU$166
21 May - 22 May
includes taxes & fees
Berkshires Untold: Pet-friendly lodge with free WiFi and free parking. Guests love the helpful staff!
Great experience

Reviewed on 13 May 2026

Opens in a new windowBerkshires Untold
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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.