Sheffield Vacations from $563
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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.
Gedney Farm
Save 100% on your flight
Price was $799, price is now $563 per person
$563
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.4/10 Exceptional! (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
Save 100% on your flight
Price was $1,723, price is now $1,026 per person
$1,026
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.8/10 Exceptional! (13 reviews)
Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay....
Reviewed on Oct 20, 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Save 100% on your flight
Price was $1,303, price is now $824 per person
$824
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.4/10 Exceptional! (110 reviews)
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!
Reviewed on Oct 27, 2025
Pocketbook Hotel and Bath
Save 100% on your flight
Price was $1,141, price is now $769 per person
$769
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
17.6/10 Exceptional! (3 reviews)
The room was nice and clean, but the hotel itself was still under construction and it took 45 minutes for us to get in our room for check-in
I was able to ask for extended check out and we got two complementary drinks from the bar but overall they should have waited to open
Reviewed on Nov 12, 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 23 to Nov 24
$161 total
Nov 23 - Nov 24
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 30 to Dec 1
$135 total
Nov 30 - Dec 1
Total with taxes and fees
9/10 Wonderful! (758 reviews)
The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway
Reviewed on Nov 14, 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 23 to Nov 24
$115 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (799 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.
