Sheffield Vacations from $395
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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.
Urban Cowboy Lodge
Save 100% on your flight
Price was $1,382, price is now $1,109 per person
$1,109
per person
Feb 18 - Feb 22
found 1 hour ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.2/10 Wonderful! (178 reviews)
Rooms need an upgrade. Staff was nice. Wish they had more dining options.
Reviewed on Nov 22, 2025
The Century House, an Ascend Collection Hotel
Price was $758, price is now $662 per person
$662
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Gulfport (GPT) to Albany (ALB)
9.2/10 Wonderful! (1,001 reviews)
The staff were super sweet and the rooms were clean. The continental breakfast was not typical and so so so much better than most hotels! We will definetly be back!
Reviewed on Dec 20, 2025
Holiday Inn Express and Suites Albany Airport- Wolf Road by IHG
Colonie
Price was $737, price is now $650 per person
$650
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Gulfport (GPT) to Albany (ALB)
8.6/10 Excellent! (1,002 reviews)
The bed was a bit too soft for us, we had a stiff back the next day. The room was very clean , reception was super friendly and helpful, water and peanuts were provided at check in for a snack and it was located less than 5 min walk to the mall across the street. Great stay.
Reviewed on Dec 24, 2025
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.
Sheffield Hotel Deals
Wilder House Berkshires
48 S Main Street Sheffield MA
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $169 total per night from Dec 30 to Dec 31
$169 total
Dec 30 - Dec 31
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
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $113 total per night from Jan 5 to Jan 6
$113 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
The bed was very comfortable. The staff was helpful and courteous
Reviewed on Dec 24, 2025
The Red Lion Inn
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
$173 nightly
The price is $194 total per night from Jan 26 to Jan 27
$194 total
Jan 26 - Jan 27, 2026
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
I had always wanted to stay at The Red Lion Inn and decided to treat myself to a one-night stay. Since it was in December I was especially excited to have a fireplace in the room. Sadly, I learned the fireplace didn’t work and that they are renovating some of the systems, but offered no partial refund ...
Reviewed on Dec 23, 2025
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
