
Sheffield Vacation Packages
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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.
Top Sheffield Vacation Deals
Price found within the past 48 hours. Click for updated prices.



Kingston Carriage House
Roundout
per person
Oct 22 - Oct 26
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (19 reviews)
I liked the record player and the room was clean and comfy. Coffee and pastries were waiting by the door in the morning. Checking in, the battery was dead in the room lock. Had to wait 30 mins for service to arrive. The shower floor was dangerously slippery! An accident waiting to happen. Was unable to connect to Wi-Fi after multiple tries.
Reviewed on Aug. 3, 2025
Sheffield Hotel Deals

Wilder House Berkshires
48 S Main Street, Sheffield, MA
Fully refundableReserve now, pay when you stay
The price is CA $221 per night from Sep 9 to Sep 10
CA $221
CA $247 total
Sep 9 - Sep 10
includes taxes & fees
9.6/10 Exceptional! (28 reviews)
"My sister and I and her husband had a very nice stay. The rooms are very nice and very clean. We enjoyed an excellent breakfast every morning. I highly recommend Wilder House!"
Reviewed on Jul. 30, 2025

Antique Farmhouse Totally Restored
Sheffield
9.8/10 Exceptional! (56 reviews)
"It was a fun place for a lot of people to stay. The only negative was the owner not having the air conditioning units in the windows of the bedrooms especially since it was so hot."
Reviewed on Jul. 14, 2025

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from Sep 7 to Sep 8
CA $106
CA $149 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (543 reviews)
"Very spacious room with full kitchen. Definitely worth the price. Would use again"
Reviewed on Aug. 5, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.