Sheffield Holidays

Book a Hotel + Flight or Car together to unlock savings

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 5.722.633 ₫ per night from 10 Jul to 11 Jul
5.722.633 ₫
6.392.181 ₫ total
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 3.083.124 ₫ per night from 14 Jul to 15 Jul
3.083.124 ₫
3.443.850 ₫ total
14 Jul - 15 Jul
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"The gentleman working at the front desk was extremely helpful when were in a pinch and needed assistance late at night! The second-level room was comfortable, clean, and quiet, and the location is amazing, just a short walk to all the restaurants, cafes and shops that downtown Great Barrington has ..."

Reviewed on 26 Jun 2025

Quality Inn
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox
2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is 2.583.405 ₫ per night from 1 Jul to 2 Jul
2.583.405 ₫
2.885.585 ₫ total
1 Jul - 2 Jul
includes taxes & fees
7.6/10 Good! (740 reviews)
"I have stayed here on and off, and even during home renovations. It’s always clean and the staff are friendly, this is one of the best kept hotels in the area!"

Reviewed on 26 Jun 2025

Howard Johnson by Wyndham Lenox
See all 1,235 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.

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

Ashley House

You can learn about the history of Sheffield when you stop by Ashley House. Discover the area's breweries or seek out the hiking trails.

Ashley House