Sheffield Holidays

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Your Sheffield Holiday

The stress-free way to experience this unique city is with a custom-made Sheffield holiday package. Stay in the neighbourhood of Canann Village Historic District, which is great for dining, culture and shopping or go someplace else — our package deals are all about you. Fill your free time with visits to Ski Butternut, Housatonic River Walk and Lake Buel, some of the things you really should see during a trip to Sheffield. Don't delay exploring this city any longer. Your ultimate Sheffield holiday is only a few clicks away with Expedia.

Sheffield Essential Information

Language
English
Currency
U.S dollars
Population
3,400
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Norman Rockwell Museum, Ski Butternut and Bash Bish Falls State Park

Top hotels in Sheffield

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street, Sheffield, MA
The price is £153 per night from 17 Aug to 18 Aug
£153
17 Aug - 18 Aug
includes taxes & fees
9.6/10 Exceptional! (28 reviews)
"My sister and I and her husband had a very nice stay. The rooms are very nice and very clean. We enjoyed an excellent breakfast every morning. I highly recommend Wilder House!"

Reviewed on 30 Jul 2025

Wilder House Berkshires
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield, MA
9.8/10 Exceptional! (56 reviews)
"It was a fun place for a lot of people to stay. The only negative was the owner not having the air conditioning units in the windows of the bedrooms especially since it was so hot."

Reviewed on 14 Jul 2025

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Antique Farmhouse Totally Restored
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (536 reviews)
"It was a great central spot for our plans in the Berkshires. The place is quiet and the staff is friendly. The rooms are very large with a stocked kitchen, dishwasher, dining table, etc. The pull out sofa has a thinner mattress so don't expect a lot of comfort, but the king bed was good. A/C could ..."

Reviewed on 31 Jul 2025

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Berkshire Mountain Lodge
See all 1,260 properties in Sheffield
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.
All Inclusive Holidays
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Popular places to visit

Magnolia Bluffs Casino

Why not roll the dice with a visit to Magnolia Bluffs Casino during your time in Sheffield? Discover the area's breweries or seek out the hiking trails.

Magnolia Bluffs Casino

Frequently asked questions

Why should I book my Sheffield holiday with Expedia?
Choose Expedia to organise your next adventure with ease, all in one place. Our top tip for bagging an unbeatable deal on a Sheffield retreat? Bundle your flights, hotel and/or hire car into a package holiday. Then throw in a few exciting tours and activities. Many bookings also come with flexible cancellation policies, so there's no need to worry if you have to change plans. Round-the-clock assistance with changing and cancelling your trip is on-hand via our Customer Service Portal link.
When is the best time of year to holiday in Sheffield?
Sheffield can get busy in February, March and May, so if you want to steer clear of the crowds, visit in October, November and December. To get an idea of what type of weather to expect, the daytime average temperature in January, the coolest time of year in Sheffield, is -5ºC. The warmest time here is July, when temperatures reach around 21ºC.
What is the top hotel for my holiday in Sheffield?
Offering many of home's creature comforts, Courtyard by Marriott Lenox Berkshires will make the ideal base for your Sheffield escape.
How do I get a cheap holiday to Sheffield?
If you love amazing deals, bundle your bookings into a Sheffield holiday. Whether you're looking for flights, hotels, tours or hire cars, you can book everything in one place. You'll have a wealth of choice at your fingertips too. Expedia has more than 400 partner airlines and 321,000 hotel options worldwide to pick from. Fly with who you prefer, find a room where you like and save your hard-earned money — now that's the perfect escape! Learn more about how you can save money on your holiday when you book a flight and hotel together with Expedia.
What should I do on my Sheffield holiday?
Offering major attractions like Ski Butternut and Bash Bish Falls State Park, a holiday in Sheffield is packed with fun things to do and see. Housatonic River Walk and Mahaiwe Performing Arts Centre are a couple of other sights worth checking out.
What is the best area to stay in when on holiday in Sheffield?
There's so much to see in Sheffield, so spend your nights near its best attractions and treat yourself to more time sightseeing. Magnolia Bluffs Casino is one place to add to your to-do list.
Do I need a visa for my Sheffield holiday?
Visa requirements for Sheffield vary depending on your nationality and purpose of your visit. Remember to check official government websites to determine if you need a visa for your trip. They'll also give you the most up-to-date information, including details about application procedures or supporting documentation you may need. Research your visa requirements well in advance to ensure a hassle-free travel experience. Also make sure your passport is valid for at least six months from the date of your return.
What should I wear on my Sheffield holiday?
Although everyone's personal style varies, it can be helpful to have a few guidelines for what kind of clothes to wear during your holiday in Sheffield. Think about browsing style blogs before you head off for inspiration on fashion trends or dress codes. Be sure to look at the local weather forecast so you can pack appropriately. The warmest time of year in Sheffield is July, with average daily temperatures of 21ºC. If you plan to visit in the coolest month of January, the mercury averages -5ºC during the day.
What does an Expedia Sheffield holiday include?
With Expedia, you can select any combination of hotels, flights and car hires to build your perfect Sheffield travel package. Once you've made your booking, simply add on the fun things like tours and activities. Don't forget, the more you bundle, the more cash you'll save! Expedia features all kinds of properties, with the most sought after in Sheffield being private holiday homes and cottages. With Expedia, you'll always have the flexibility and freedom to design your holiday however you like.
Does Expedia offer Book Now, Pay Later Sheffield holidays?
Yes. Expedia has partnered with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply click on the payment plan that works for you during checkout and take the stress out of budgeting for your next trip. Remember to bundle your flights, hotel and car hire with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's manageable monthly instalment plans. If paying bite-sized amounts each month sounds right for you, choose this option at checkout.
  • No-deposit holidays: When you want to jump on an amazing deal but your budget doesn't quite cover it yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your getaway.

Can I choose my airline with a Sheffield Expedia holiday?
Most definitely. Expedia has over 400 partner airlines to choose from worldwide. With such a huge range of choices, finding the ideal carrier to whisk you off to Sheffield shouldn't be hard.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.