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
The price is S$195 per night from 10 Jul to 11 Jul
S$195
10 Jul - 11 Jul
includes taxes & fees
9.6/10 Exceptional! (25 reviews)
Lovely stay
"Brad was a terrific host in a perfect location to explore northwestern Connecticut and the Berkshires."

Reviewed on 16 Jun, 2025

Wilder House Berkshires
Quality Inn
Quality Inn
2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is S$169 per night from 9 Jul to 10 Jul
S$169
9 Jul - 10 Jul
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"It was clean and comfortable and a great location. Breakfast was good. Staff were helpful and pleasant."

Reviewed on 22 Jun, 2025

Quality Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
The price is S$229 per night from 30 Jun to 1 Jul
S$229
30 Jun - 1 Jul
includes taxes & fees
9/10 Wonderful! (659 reviews)
Good for a girls trip!
"We loved the comfortable beds and ensuite bathrooms. The kitchen was well-equipped and common room was comfortable too. We didn't use any of the other amenities, but there were quite a few options that looked appealing. Convenient to Lenox which was our primary destination for dining and ..."

Reviewed on 21 Jun, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 1,233 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.