Sheffield Holiday Packages

Save when you book Sheffield package deals

Choose two or more items and save on your trip:

Book your Sheffield holiday

Save some moolah with Wotif.

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

Sheffield is waiting!

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 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$274 per night from 30 Dec to 31 Dec
AU$274
30 Dec - 31 Dec
includes taxes & fees
Wilder House Berkshires: Bed & breakfast with free breakfast and free WiFi.
Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you!

Reviewed on 10 Nov 2025

Opens in a new windowWilder House Berkshires
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield MA
Antique Farmhouse Totally Restored : Family-friendly holiday home with free WiFi and 1 hot tub. Located near theme parks.
Remarkable house! I'm still agape at the beauty of the spalted maple woodwork in the kitchen and front area of the place! Plenty of wood for the stoves kept us really warm. Feeding your Highland cows was a highlight for the little folks!

Reviewed on 5 Dec 2025

Opens in a new windowAntique Farmhouse Totally Restored
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is AU$156 per night from 1 Jan to 2 Jan
AU$156
1 Jan - 2 Jan 2026
includes taxes & fees
The Yankee, Trademark Collection by Wyndham: Business-friendly hotel with free breakfast and free WiFi. Located near skiing.
Great spot

Reviewed on 15 Dec 2025

Opens in a new windowThe Yankee, Trademark Collection by Wyndham
Don't see what you're looking for?
See all available properties in Sheffield
View all properties
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.