Sheffield Vacations from $479

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Your Sheffield Vacation

The stress-free way to experience this unique city is with a custom-made Sheffield vacation package. Stay in the neighborhood of Canann Village Historic District, which is great for dining, culture and shopping or go someplace else — our package deals are all about you. Fill your free time with visits to Ski Butternut, Housatonic River Walk and Lake Buel, some of the things you really should see during a trip to Sheffield. Don't delay exploring this city any longer. Your ultimate Sheffield vacation is only a few clicks away with Expedia.

The Latest Sheffield vacation packages

Price found within the past 48 hours. Click for updated prices.
Albany Airport Inn

Albany Airport Inn

2.5 out of 5
Price was $557, price is now $479 per person
$479
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
6.6/10 (1,006 reviews)

Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $946, price is now $786 per person
$786
per person
Jan 22 - Jan 26
just found
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.4/10 Exceptional! (22 reviews)
The place was clean and beautiful. You need to check with Expedia . I didn’t get the steps to get in, since there is nobody on site. to check in. I call the phone on site. Somebody call me back and walk me through step to get in.

Reviewed on Oct 19, 2026

The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Nothside
Price was $807, price is now $680 per person
$680
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)

Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
Downtown Albany
Price was $746, price is now $646 per person
$646
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
9.2/10 Wonderful! (1,901 reviews)

The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

4.5 out of 5
Manchester Village Historic District
Price was $689, price is now $619 per person
$619
per person
Jan 22 - Jan 26
just found
Roundtrip flight included
New York (NYC) to Albany (ALB)
7.4/10 Good! (672 reviews)

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Stay near popular Sheffield attractions

Ashley House

Built in 1735, the Ashley House is where Elizabeth Freeman successfully sued for her freedom, helping end slavery in Massachusetts. Tour the historic rooms and learn about this pivotal chapter in American history.
See properties

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
$189 nightly
The price is $211 total per night from Nov 2 to Nov 3
$211 total
Nov 2 - Nov 3
Total with taxes and fees
9.8/10 Exceptional! (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."

Reviewed on Oct 19, 2026

Wilder House Berkshires
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield MA
Get rates
Antique Farmhouse Totally Restored
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from Dec 2 to Dec 3
$126 total
Dec 2 - Dec 3
Total with taxes and fees
Berkshire Mountain Lodge
See all 1,278 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.

Find the Best Sheffield Vacation Packages

Sheffield Essential Information

Language
English
Currency
U.S dollars
Population
3,400
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Bash Bish Falls State Park, Umpachene Falls Park and Mount Everett State Reservation

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Frequently asked questions

How much does a Sheffield vacation package cost?
You can snap up a vacation package to this popular destination from $479 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?
October, November and December are the best times to look for cheap Sheffield vacation packages. Choosing to travel in quieter months means you can generally find reduced prices on flights and accommodations.
How many days is enough for Sheffield?
The ideal length for your Sheffield vacation depends on what you'd like to see and do. Typically, a few days to a week will give you time to tick off all the main attractions and discover some hidden spots along the way.
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.
Does Expedia offer Book Now, Pay Later Sheffield vacation packages?
If you're like us, you love discovering new places but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Sheffield vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.