Sheffield Vacations from $400

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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.
The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Nothside
Price was $579, price is now $400 per person
$400
per person
Jun 1 - Jun 4
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.2/10 Wonderful! (1,004 reviews)
Clean room. Courteous and professional staff.

Reviewed on Mar 11, 2026

Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

3 out of 5
Save 100% on your flight
Price was $8,698, price is now $6,382 per person
$6,382
per person
May 24 - May 28
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
No reviews
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3 out of 5
Save 100% on your flight
Price was $1,847, price is now $1,445 per person
$1,445
per person
May 24 - May 28
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
No reviews
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

3 out of 5
Save 100% on your flight
Price was $2,548, price is now $2,027 per person
$2,027
per person
May 24 - May 28
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
No reviews
Marriott Albany

Marriott Albany

3.5 out of 5
Price was $660, price is now $538 per person
$538
per person
Jun 1 - Jun 4
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.4/10 Very Good! (878 reviews)
Everything was fine except for the bedding. All the pillows smelled like body odor bad. I can’t figure out how the cleaner didn’t smell them when changing the bedding. I didn’t use them and their systems were down soo their phone wasn’t working to call the desk. Everything else was fine.

Reviewed on Mar 10, 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
$146 nightly
The price is $163 total per night from Mar 17 to Mar 18
$163 total
Mar 17 - Mar 18
Total with taxes and fees
9.8/10 Exceptional! (43 reviews)
Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back.

Reviewed on Jan 23, 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! (14 reviews)
Great quiet house.

Reviewed on Oct 17, 2025

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
$115 nightly
The price is $128 total per night from Apr 12 to Apr 13
$128 total
Apr 12 - Apr 13
Total with taxes and fees
9/10 Wonderful! (872 reviews)
the room was huge - we loved it!!

Reviewed on Mar 11, 2026

Berkshire Mountain Lodge
See all 1,285 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 $400 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.