Sheffield Trips (flight + hotel)

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    Better together
    Save up to P 3,118 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Sheffield

Wilder House Berkshires
Wilder House Berkshires
2 out of 5
48 S Main Street, Sheffield, MA
The price is P8,747 per night from Jun 30 to Jul 1
P8,747
P9,770 total
Jun 30 - Jul 1
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 Jun 16, 2025

Wilder House Berkshires
Quality Inn
Quality Inn
2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is P6,232 per night from Jun 24 to Jun 25
P6,232
P6,961 total
Jun 24 - Jun 25
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Clean, quiet hotel in Great Barrington. Staff members were kind and attentive. Easy parking and check in / check out."

Reviewed on Jun 17, 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
The price is P7,152 per night from Jun 24 to Jun 25
P7,152
P8,787 total
Jun 24 - Jun 25
includes taxes & fees
9/10 Wonderful! (658 reviews)
"Well run, clean, and comfortable."

Reviewed on Jun 16, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 1,241 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 many days is enough for Sheffield?
Usually, a handful of days is enough to check out the main attractions during your Sheffield vacation. 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 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.

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