Sheffield Vacations from $569

Book a Hotel + Flight or Car together to unlock savings

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.
Gedney Farm

Gedney Farm

3.5 out of 5
Price was $789, price is now $569 per person
$569
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.2/10 Wonderful! (132 reviews)
My wife and I chose Gedney Farms at the last minute to enjoy a quick escape from the city. The staff was friendly and welcoming. The checkin and checkout experience was seamless. The room had a truly rustic charm, and clean and orderly. In the morning we took a nice walk on the grounds. For a quick and relaxing getaway, Gedney Farms is a great choice.

Reviewed on Nov 2, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $997, price is now $637 per person
$637
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9.4/10 Exceptional! (13 reviews)
Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession.

Reviewed on Nov 29, 2025

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Price was $927, price is now $664 per person
$664
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.8/10 Excellent! (3 reviews)
The front desk was very helpful in making sure we had a good stay.

Reviewed on Jan 9, 2026

Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater Sunny Pond

Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater Sunny Pond

3 out of 5
Save 100% on your flight
Price was $4,008, price is now $2,960 per person
$2,960
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
No reviews
The Dewey

The Dewey

3.5 out of 5
Price was $825, price is now $612 per person
$612
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.6/10 Excellent! (329 reviews)
Great spot. Lots of history.

Reviewed on Sep 12, 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
$179 nightly
The price is $200 total per night from Jan 19 to Jan 20
$200 total
Jan 19 - Jan 20
Total with taxes and fees
9.8/10 Exceptional! (41 reviews)
The place is lovely, room is cozy, and the bed is comfy

Reviewed on Dec 22, 2025

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
$130 nightly
The price is $145 total per night from Feb 1 to Feb 2
$145 total
Feb 1 - Feb 2
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 $569 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.