Sheffield Vacations from $365
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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 Landing Hotel at Rivers Casino & Resort
Stockade Historic District
Price was $467, price is now $365 per person
$365
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.2/10 Wonderful! (1,006 reviews)
Liked the view from my windows and the room service breakfast was wonderful
Reviewed on Nov 12, 2025
The Equinox Golf Resort & Spa
Price was $1,017, price is now $756 per person
$756
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
7.4/10 Good! (549 reviews)
Nice room, comfortable bed. This is an old grand hotel in tip top shape. We often stay in this type of hotel in NH and VT and found the Equinox to be the best maintained of them all. All the architectural class of its age in virtually new condition. Nice, reasonably priced onsite dining. We didn’t use the large indoor pool but it looked first class. Pleasant staff. We hope to return. Recommend “Ok for breakfast”, a 2nd floor breakfast & lunch restaurant downtown.
Reviewed on Oct 27, 2025
Hotel Brookmere & Arbor Spa
Price was $541, price is now $405 per person
$405
per person
Dec 30 - Jan 2
found 8 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
9/10 Wonderful! (185 reviews)
Room spotless. However no cups in bathroom. Wine chiller did not work and had to be replaced. Also had to request clothing hangers for clothing. Only two hangers were in room.
Reviewed on Nov 9, 2025
Vacation Village in the Berkshires
Price was $753, price is now $568 per person
$568
per person
Dec 27 - Dec 31
found 9 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
8.6/10 Excellent! (2,062 reviews)
Best of the Berkshires! Clean, Comfortable and convenient. Parking is a bit weird and cramped but not overshadowing the room itself.
Reviewed on Nov 10, 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
$144 nightly
The price is $161 total per night from Nov 16 to Nov 17
$161 total
Nov 16 - Nov 17
Total with taxes and fees
9.6/10 Exceptional! (38 reviews)
Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you!
Reviewed on Nov 10, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $135 total per night from Nov 16 to Nov 17
$135 total
Nov 16 - Nov 17
Total with taxes and fees
9/10 Wonderful! (750 reviews)
Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome.
Reviewed on Nov 4, 2025
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $115 total per night from Nov 16 to Nov 17
$115 total
Nov 16 - Nov 17
Total with taxes and fees
9/10 Wonderful! (797 reviews)
Enjoyed the Clubhouse before retiring in for the evening. Cozy, comfortable, and relaxing atmosphere.
Reviewed on Nov 10, 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.