Sheffield Holiday Packages

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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 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

Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield
Antique Farmhouse Totally Restored : Family-friendly holiday home with free WiFi and 1 hot tub. Located near skiing.
Lovely, spacious, comfortable House...
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily ..."

Reviewed on 23 Sep. 2024

Antique Farmhouse Totally Restored
Race Brook Lodge

Race Brook Lodge

2 out of 5
864 S Undermountain Rd, Sheffield, MA
Race Brook Lodge : Hotel with free WiFi and free parking.
"Amazing experience in every aspect!"

Reviewed on 28 Oct. 2024

Race Brook Lodge
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Sheffield
The price is AU$820 per night from 5 Jan to 6 Jan
AU$820
includes taxes & fees
5 Jan - 6 Jan 2025
Cheerful 3-bedroom cottage with woodstove: Pet-friendly holiday home with free WiFi and a fitness centre. Located near skiing.
Second Stay
"We stayed at this home about the same time last year and we were so happy with everything about it, we jumped at the opportunity to stay there again. The house has absolutely everything you'd need and is close to Canaan, CT and Great Barrington, MA and everything the Bershires have to offer. Sabrina ..."

Reviewed on 5 Dec. 2024

Cheerful 3-bedroom cottage with woodstove
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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.