Sheffield Vacations from $319

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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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Save 100% on your flight
per person
Sep 13 - Sep 20
found 12 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
8.6/10 Excellent! (1,862 reviews)
Wonderful property in an idyllic setting! Everything you need for a quality vacation with friends or family. One of the most relaxing getaways I've ever had.

Reviewed on Jul 11, 2025

Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Save 100% on your flight
per person
Sep 21 - Sep 25
found 17 hours ago
Roundtrip non-stop flight included
New York (NYC) to Albany (ALB)
9.4/10 Exceptional! (463 reviews)
Wonderful trip and wonderful resort!

Reviewed on Jul 1, 2025

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
per person
Aug 15 - Aug 18
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9/10 Wonderful! (1,000 reviews)
Cornell Inn was lovely. The place is so clean- and I’m a germaphobe! The staff was kind, helpful and welcoming. The breakfast was delicious and served outside in a beautiful garden. Would definitely recommend.

Reviewed on Jul 7, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
7.4/10 Good! (486 reviews)
Just love the very historic sence

Reviewed on Jul 6, 2025

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
Save 100% on your flight
per person
Sep 13 - Sep 20
found 12 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
Great service and a wonderful place to stay

Reviewed on Jul 9, 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
Fully refundableReserve now, pay when you stay
$225 nightly
The price is $251 total per night from Jul 21 to Jul 22
$251 total
Jul 21 - Jul 22
Total includes taxes and fees
9.6/10 Exceptional! (26 reviews)
Lovely stay
"Brad was a terrific host in a perfect location to explore northwestern Connecticut and the Berkshires."

Reviewed on Jun 16, 2025

Wilder House Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $170 total per night from Jul 16 to Jul 17
$170 total
Jul 16 - Jul 17
Total includes taxes and fees
9/10 Wonderful! (670 reviews)
"Rooms need renovation but a nice property"

Reviewed on Jul 11, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Berkshires Untold
Berkshires Untold
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $223 total per night from Jul 14 to Jul 15
$223 total
Jul 14 - Jul 15
Total includes taxes and fees
9/10 Wonderful! (629 reviews)
"Property is decorated beautifully. The outdoor space is excellent. Overall a great find. Ill stay again if i go to Tanglewood"

Reviewed on Jul 9, 2025

Berkshires Untold
See all 1,246 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 $319 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.