Sheffield Vacations from $393
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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
Save 100% on your flight
Price was $595, price is now $393 per person
$393
per person
May 4 - May 11
found 4 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.8/10 Excellent! (2,134 reviews)
Great! Go annually. Highly recommend
Reviewed on Feb 25, 2026
Hilton Garden Inn Saratoga Springs
Save 100% on your flight
Price was $1,052, price is now $792 per person
$792
per person
May 14 - May 19
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8/10 Very Good! (1,003 reviews)
The sink aerator is too powerful and it splashes water on your belly (or pants). You can't really adjust it. I get it that they are trying to save water, but they need to find a better model (or clean the one installed).
There is no towel rack in easy reach of the shower.
One of the dresser table lamps did not work.
Reviewed on Feb 16, 2026
Hotel Brookmere & Arbor Spa
Save 100% on your flight
Price was $792, price is now $599 per person
$599
per person
May 14 - May 19
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9.2/10 Wonderful! (218 reviews)
Everything was fine. The only exception we had to leave because of the weather . When we asked f we can get a refund , the manager declined. I guess he or she was worried about there numbers .
Reviewed on Feb 24, 2026
Bluebird Spa City Motor Lodge
Downtown Saratoga Springs
Save 100% on your flight
Price was $958, price is now $726 per person
$726
per person
May 14 - May 19
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9/10 Wonderful! (801 reviews)
I’ve stayed at this location many times. The lodging is perfectly located in the heart of everything. Walking distance to food, shopping, and activities. The lodging itself is affordable, clean, and welcoming. A great place to stay!
Reviewed on Feb 11, 2026
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
$184 nightly
The price is $206 total per night from Mar 8 to Mar 9
$206 total
Mar 8 - Mar 9
Total with taxes and fees
9.8/10 Exceptional! (43 reviews)
Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back.
Reviewed on Jan 23, 2026
Guesthouse Cabin vacation rentals in Berkshire County
Sheffield MA
$627 nightly
The price is $700 total per night from Mar 2 to Mar 3
$700 total
Mar 2 - Mar 3
Total with taxes and fees
10/10 Exceptional! (10 reviews)
We were a group of moms who snuck away for the night and this cabin was the perfect retreat. Well stocked and very cozy on a winter night. We had to leave very early the next morning to beat a snowstorm and the very long driveway was already sanded and we felt very safe. Lisette was great to work ...
Reviewed on Jan 29, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $158 total per night from Mar 27 to Mar 28
$158 total
Mar 27 - Mar 28
Total with taxes and fees
9/10 Wonderful! (863 reviews)
Overall pleasant stay; great facilities, staff, and location
Reviewed on Feb 24, 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
