Sheffield Vacations from $556

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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.
Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $649, price is now $556 per person
$556
per person
Jan 21 - Jan 24
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
8.8/10 Excellent! (600 reviews)
Our room was large and very clean. Just a cozy feel

Reviewed on Dec 16, 2025

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Nothside
Price was $804, price is now $603 per person
$603
per person
Feb 8 - Feb 12
found 19 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
Everything about our stay was perfect! The lady at check-in was super friendly, the room was extremely clean and modern. Definitely recommend The Landing!

Reviewed on Nov 23, 2025

The Manchester View

The Manchester View

2.5 out of 5
Price was $966, price is now $737 per person
$737
per person
Jan 21 - Jan 24
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
9.4/10 Exceptional! (772 reviews)
Room very clean comfortable and quiet

Reviewed on Dec 13, 2025

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 $722, price is now $614 per person
$614
per person
Feb 8 - Feb 12
found 19 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
8.4/10 Very Good! (1,004 reviews)
Everything was great except we stayed 4 nights and never once was our room cleaned or towels refreshed.

Reviewed on Dec 7, 2025

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $727, price is now $626 per person
$626
per person
Feb 8 - Feb 12
found 19 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
8.8/10 Excellent! (1,001 reviews)
Clean room, amenities, staff

Reviewed on Dec 5, 2025

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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
$150 nightly
The price is $168 total per night from Dec 17 to Dec 18
$168 total
Dec 17 - Dec 18
Total with taxes and fees
9.6/10 Exceptional! (38 reviews)
Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you!

Reviewed on Nov 10, 2025

Wilder House Berkshires
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield MA
9.6/10 Exceptional! (60 reviews)
Remarkable house! I'm still agape at the beauty of the spalted maple woodwork in the kitchen and front area of the place! Plenty of wood for the stoves kept us really warm. Feeding your Highland cows was a highlight for the little folks!

Reviewed on Dec 5, 2025

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Antique Farmhouse Totally Restored
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
$93 nightly
The price is $103 total per night from Dec 24 to Dec 25
$103 total
Dec 24 - Dec 25
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
The room was fantastic, cozy as can be! Also, as soon as you walk into the lobby it looked wonderful! The Manager, Jennifer was so nice to talk too! She made sure everything with room, etc. was good! She was a delight!

Reviewed on Dec 12, 2025

The Yankee, Trademark Collection by Wyndham
See all 1,266 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 $556 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.