Sheffield Holiday Packages

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We can bundle your flights and accommodation into a simple package.

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How does an additional sound? That's what you could save if you book now. And don't forget — you've got the flexibility to mix and match from more than 550 airlines and 665,000 properties.

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 accommodation 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

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield
The price is NZ$1,454 per night from 21 Apr to 22 Apr
NZ$1,454
includes taxes & fees
21 Apr - 22 Apr
Stay at this cabin in Sheffield. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Mount Everett State Reservation and Plaintain Pond ...
Comfort and Views
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private."

Reviewed on 2 Sep. 2024

Guesthouse Cabin vacation rentals in Berkshire County
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 NZ$286 per night from 27 Apr to 28 Apr
NZ$286
includes taxes & fees
27 Apr - 28 Apr
Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife ...
"Bert was great - he really tried to help after the Expedia website (and app) made it impossible for me to cancel my trip (my wife and I came down with Influenza A). There was little he could do as I had booked through Expedia. I ended up paying full price and am finding it impossible to communicate ..."

Reviewed on 14 Apr. 2025

Wilder House Berkshires
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$241 per night from 22 Apr to 23 Apr
NZ$241
includes taxes & fees
22 Apr - 23 Apr
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
"The hotel is cozy and charming. The rooms are well-appointed. The staff was great. Easy check-in, check-out. The bar is well stocked and they offer free (real) coffee in the morning!"

Reviewed on 14 Apr. 2025

Life House Berkshires
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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.