Sheffield Vacations from $324

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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.
Red Roof Inn Clifton Park

Red Roof Inn Clifton Park

2 out of 5
Price was $367, price is now $324 per person
$324
per person
Feb 3 - Feb 7
found 17 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
7.2/10 Good! (1,001 reviews)
Very clean room and corteous staff.

Reviewed on Jan 1, 2026

Hampton Inn Clifton Park

Hampton Inn Clifton Park

2.5 out of 5
Price was $438, price is now $366 per person
$366
per person
Feb 3 - Feb 7
found 17 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
9.2/10 Wonderful! (1,002 reviews)
The staff were nice and the room was clean.

Reviewed on Dec 14, 2025

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Nothside
Price was $606, price is now $527 per person
$527
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
Clean room, great heat, everything worked. Easy (free) parking. Great overall stay.

Reviewed on Dec 29, 2025

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $539, price is now $488 per person
$488
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
8.8/10 Excellent! (1,001 reviews)
the heating system is very noisy and very difficult to fall asleep

Reviewed on Jan 1, 2026

The Clocktower Hotel at Century House, an Ascend Collection Hotel

The Clocktower Hotel at Century House, an Ascend Collection Hotel

2.5 out of 5
Price was $519, price is now $475 per person
$475
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
8.4/10 Very Good! (1,004 reviews)
Room was clean, comfortable, and affordable. Staff was exceptionally accommodating. Breakfast was as good as ones we paid $30 per person. This hotel is a great value.

Reviewed on Jan 1, 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
$176 nightly
The price is $197 total per night from Jan 22 to Jan 23
$197 total
Jan 22 - Jan 23
Total with taxes and fees
9.8/10 Exceptional! (41 reviews)
The place is lovely, room is cozy, and the bed is comfy

Reviewed on Dec 22, 2025

Wilder 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
$101 nightly
The price is $113 total per night from Jan 11 to Jan 12
$113 total
Jan 11 - Jan 12
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
The room was clean, comfortable and spacious. The bathroom had enough space and was clean and well appointed.

Reviewed on Dec 30, 2025

The Yankee, Trademark Collection by Wyndham
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 Feb 1 to Feb 2
$120 total
Feb 1 - Feb 2
Total with taxes and fees
9/10 Wonderful! (800 reviews)
great stall and friendly pet friendly place

Reviewed on Dec 31, 2025

Berkshire Mountain Lodge
See all 1,267 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 $324 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.