Sheffield Vacations from $659

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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.
Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

2.5 out of 5
Price was $794, price is now $659 per person
$659
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
8.4/10 Very Good! (1,000 reviews)
Hotel was very nice and clean. Staff was very friendly

Reviewed on Apr 10, 2026

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $936, price is now $702 per person
$702
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
8.8/10 Excellent! (1,008 reviews)
Not bad for a place to sleep after a flight.

Reviewed on Apr 11, 2026

Hilton Garden Inn Saratoga Springs

Hilton Garden Inn Saratoga Springs

3 out of 5
Price was $876, price is now $708 per person
$708
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
8/10 Very Good! (1,004 reviews)
The breakfast was wonderful. All the Hostesses and Staff have exceptional customer service skills and have exceeded my expectations.

Reviewed on Apr 11, 2026

Hilton Albany

Hilton Albany

3.5 out of 5
Downtown Albany
Price was $857, price is now $713 per person
$713
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
7.2/10 Good! (1,005 reviews)
Picked this property for walkability to the egg. Staff was great, room appeared clean, but we found bed bugs in the morning in one of the beds. Would not stay again.

Reviewed on Apr 12, 2026

The Century House Latham - North Albany, an Ascend Collection Hotel

The Century House Latham - North Albany, an Ascend Collection Hotel

3 out of 5
Price was $832, price is now $711 per person
$711
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
9.2/10 Wonderful! (1,002 reviews)
The staff is very nice and the breakfast was good. The facility was old and run down.

Reviewed on Apr 5, 2026

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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

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
$149 nightly
The price is $166 total per night from Apr 22 to Apr 23
$166 total
Apr 22 - Apr 23
Total with taxes and fees
9.8/10 Exceptional! (44 reviews)
Only discomfort was a hard rug on my barefeet. So I'll remember to bring slippers. Otherwise, the ambiance, service, friendliness, access was wonderful. What a lovely place!

Reviewed on Apr 3, 2026

Wilder House Berkshires
Luxury Private Estate in the Berkshires | Whitney by AvantStay

Luxury Private Estate in the Berkshires | Whitney by AvantStay

Sheffield MA
8.6/10 Excellent! (15 reviews)
We had a lovely stay. Wonderfully located and well provisioned! Would happily stay here again!

Reviewed on Mar 29, 2026

Get rates
Luxury Private Estate in the Berkshires | Whitney by AvantStay
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from May 11 to May 12
$120 total
May 11 - May 12
Total with taxes and fees
9/10 Wonderful! (904 reviews)
Great all clean and nice place

Reviewed on Apr 12, 2026

Berkshire Mountain Lodge
See all 1,300 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 $659 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.