Sheffield Vacations from $471
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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.
Lodges At Cresthaven
$471
per person
Nov 19 - Nov 22
found 10 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.4/10 Exceptional! (628 reviews)
They have pocket doors on the bathrooms with no locks. The slope of the property was so great that my reasonably healthy wife could not access the beach area. The property is beautiful, but in my opinion it is not well suited for older adults.
Reviewed on Aug 27, 2026
The Cornell Inn, Lenox & The Berkshires
$1,202
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Albany (ALB)
9.2/10 Wonderful! (1,007 reviews)
Lovely people and place. Breakfast was great and so was the room. Highly recommend.
Reviewed on Aug 31, 2026
Kingston Regency Inn
$494
per person
Nov 19 - Nov 23
found 19 hours ago
Roundtrip flight included
Minneapolis (MSP) to Albany (ALB)
7.4/10 Good! (1,004 reviews)
We could hear the sound from the hallway and from next door very clearly when we stayed there. We arrived around 1:40pm which was 1 and 20 minutes earlier than 3pm official check in time and was charged $25 for early check in. The room was already available but the staff told us we either coming back 1 hour later or we pay $25 for early check in which was nonsense . I booked the hotel through expedia but the hotel staff told me their record shows my reservation booked directly from them. Not sue whose fault it was, but I got double charged by both expedia and the hotel. I showed the staff my experdia reservation receipt, but he refused to contact expedia to solve the problem. Instead he insisted me to pay the full amount plus the $25 early check in fee and ask me to call expedia myself. It felt pretty cold.
Reviewed on Aug 31, 2026
Stay near popular Sheffield attractions
Ashley House
Built in 1735, the Ashley House is where Elizabeth Freeman successfully sued for her freedom, helping end slavery in Massachusetts. Tour the historic rooms and learn about this pivotal chapter in American history.
Thom Reed UFO Monument Park
8.0/10 (1 review)
America's first officially documented UFO encounter is commemorated at this riverside park in Sheffield. Explore plaques about the Reed family's 1969 experience while enjoying Housatonic River views.
Bartholomews Cobble
Twin rocky knolls form this National Natural Landmark, home to one of North America's most diverse fern collections. Explore five miles of trails through forests and riverbanks for exceptional wildlife viewing.
Drury Preserve
Explore diverse ecosystems along a serene 2.4-mile trail through hemlock forests and calcareous wetlands. Cross wooden boardwalks to a tranquil pond where great blue herons and other wildlife await.
Lime Kiln Farm Wildlife Sanctuary
This wildlife sanctuary showcases diverse plant species across limestone ridges and conifer forests. Explore trails to spot numerous butterfly species and Pileated Woodpeckers in the tranquil Berkshires landscape.
Bartholomew's Cobble
10.0/10 (1 review)
This National Natural Landmark features twin rocky knolls and North America's most diverse fern collection. Explore its trails through varied ecosystems while watching for peregrine falcons and rare plants.
Sheffield Hotel Deals
Wilder House Berkshires
48 S Main Street Sheffield MA
Fully refundableReserve now, pay when you stay
$206 nightly
$231 total
Sep 13 - Sep 14
Total with taxes and fees
9.8/10 Exceptional! (62 reviews)
"Breakfast was delicious and everyone was so nice there."
Reviewed on Aug 18, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$108 nightly
$120 total
Oct 1 - Oct 2
Total with taxes and fees
9/10 Wonderful! (1,107 reviews)
"Clean & comfortable stay"
Reviewed on Aug 31, 2026
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 $471 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.
