Sheffield Vacations

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Find the Best Sheffield Vacation Packages

Sheffield Hotel Deals

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 AED 562 per night from Apr 8 to Apr 9
AED 562
AED 628 total
includes taxes & fees
8 Apr - 9 Apr
9.8/10 Exceptional! (17 reviews)
"I’m a returning guest. The house is always charming, welcoming, comfortable and clean! The owner is very accommodating."

Reviewed on 7 March 2025

Wilder House Berkshires
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AED 355 per night from Apr 16 to Apr 17
AED 355
AED 397 total
includes taxes & fees
16 Apr - 17 Apr
9/10 Wonderful! (539 reviews)
"Enjoyed having an excellent meal and bar was very convenient."

Reviewed on 30 March 2025

Life House Berkshires
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 AED 325 per night from Apr 14 to Apr 15
AED 325
AED 363 total
includes taxes & fees
14 Apr - 15 Apr
9/10 Wonderful! (1,003 reviews)
Great but firm mattress
"Great location and the room was very nice. The only issue I had was the bed was very firm."

Reviewed on 2 April 2025

The Yankee, Trademark Collection by Wyndham
See all 1,193 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 vacation package cost?
You can snap up a vacation package to this popular destination on Expedia. But how much your vacation 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 vacation packages? Try to avoid visiting during public holidays and any major festivals or events.
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 vacation package as soon as possible.
Is it cheaper to book a Sheffield vacation as a package?
You can enjoy significant savings on your Sheffield escape by booking a customized vacation package. Check the “Package” heading, then enter your destination and travel dates to see the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation 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 accommodations and airfare: After you’ve settled on your trip dates and duration, book the perfect Sheffield vacation package for you.

Discover the most popular places to visit in Sheffield

Magnolia Bluffs Casino

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

Magnolia Bluffs Casino

Ashley House

You can learn about the history of Sheffield with a trip to Ashley House. Discover the area's breweries or seek out the hiking trails.

Ashley House