Sheffield Vacations from $292

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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 Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $365, price is now $292 per person
$292
per person
Feb 26 - Mar 1
found 21 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
9.4/10 Exceptional! (162 reviews)
Great stay! Well decorated and a beautiful building walking distance from shops restos and the beautiful downtown. The host was waiting to greet us even though we were quite late to check in. Would stay again!

Reviewed on Dec 30, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Price was $989, price is now $750 per person
$750
per person
Feb 27 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
7.4/10 Good! (567 reviews)
The resort really needs updating....

Reviewed on Jan 14, 2026

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Nothside
Price was $767, price is now $589 per person
$589
per person
Mar 12 - Mar 15
found 21 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
I also have a nice time at this hotel it's friendly convenient and clean I wish they had more food choices and more things to do but always nice to stay here. I'm exited for my next trip.

Reviewed on Jan 13, 2026

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

3 out of 5
Save 100% on your flight
Price was $718, price is now $580 per person
$580
per person
Feb 26 - Mar 1
found 21 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
No reviews
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $738, price is now $605 per person
$605
per person
Feb 27 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9.6/10 Exceptional! (11 reviews)
Great property. Amazing views!

Reviewed on Dec 2, 2024

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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
$178 nightly
The price is $199 total per night from Jan 28 to Jan 29
$199 total
Jan 28 - Jan 29
Total with taxes and fees
9.8/10 Exceptional! (42 reviews)
It was a very pleasant hybrid of a classic BnB with the privacy of an air BnB. Host was on point and communicative. We loved hanging out downstairs in the living room(s). Breakfast was fabulous

Reviewed on Jan 14, 2026

Wilder House Berkshires
Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield MA
$621 nightly
The price is $694 total per night from Jan 19 to Jan 20
$694 total
Jan 19 - Jan 20
Total with taxes and fees
10/10 Exceptional! (9 reviews)
This was exactly what we were looking for. The property was magnificent the cabin cozy, fully stocked. We plan on coming back soon.

Reviewed on Aug 27, 2025

Guesthouse Cabin vacation rentals in Berkshire County
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $136 total per night from Feb 16 to Feb 17
$136 total
Feb 16 - Feb 17
Total with taxes and fees
9/10 Wonderful! (810 reviews)
Very comfortable and very close to ski slope and restaurants

Reviewed on Jan 10, 2026

Berkshire Mountain Lodge
See all 1,254 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 $292 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.