Sheffield Holidays

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Top hotels in Sheffield

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 €190 per night from 17 Aug to 18 Aug
€190
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
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
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is €409 per night from 8 Aug to 9 Aug
€409
8 Aug - 9 Aug
includes taxes & fees
9/10 Wonderful! (654 reviews)
"Very nice hotel, convenient location to Tanglewood and other attractions. Quiet and comfortable beds."

Reviewed on 30 Jul 2025

Berkshires Untold
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.

Frequently asked questions

How much does a Sheffield holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. But how much your holiday to Sheffield costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Sheffield?
The off-season is the best time to visit Sheffield if you're trying to keep costs down. Another tip for getting cheap Sheffield holiday packages? Try to avoid visiting during public holidays and any major festivals or events.
How many days is enough for Sheffield?
Usually, a handful of days is enough to check out the main attractions during your Sheffield holiday. But if you prefer to have time to unwind or take day tours, think about extending your trip.
How to find the best Sheffield package deals?
Use Expedia's filters to find some terrific Sheffield package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Sheffield package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book a Sheffield holiday as a package?
You can enjoy significant savings on your Sheffield escape by booking a customised holiday package. Check the "Package" heading, then enter your destination and travel dates to see the best hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Sheffield?
If you're considering an impromptu Sheffield getaway, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Sheffield?

  1. Choose when to go: Check your calendar and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to visit Sheffield.
  2. Set a budget: Consider expenses like flights, food and transportation when working out how much to save for your trip to Sheffield. Then, pick a hotel that suits your budget, whether that's a low-cost stay or a more upscale getaway.
  3. Work out your trip length: Think about how long you want to spend discovering Sheffield. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your accommodation and airfare: After you've settled on your trip dates and duration, book the perfect Sheffield holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.