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.
The Manchester View
Price was CA $1,202, price is now CA $1,062 per person
CA $1,062
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9.4/10 Exceptional! (818 reviews)
Beautiful property, clean room, friendly staff. Will definitely be staying here again!
Reviewed on Mar 18, 2026
Hotel Brookmere & Arbor Spa
Price was CA $1,877, price is now CA $1,591 per person
CA $1,591
per person
May 15 - May 19
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Albany (ALB)
9.2/10 Wonderful! (271 reviews)
Located by the elevator was a bit noisy. Other than that, wonderful stay!
Reviewed on Mar 11, 2026
Hyatt Place Albany/Downtown
Downtown Albany
Price was CA $1,947, price is now CA $1,740 per person
CA $1,740
per person
May 15 - May 19
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Albany (ALB)
9/10 Wonderful! (1,519 reviews)
Wonderful staff and hotel! We would definitely stay again if we’re in the area.
Reviewed on Mar 29, 2026
Sheffield Hotel Deals
Wilder House Berkshires
48 S Main Street Sheffield MA
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from Apr 5 to Apr 6
CA $202
CA $225 total
Apr 5 - Apr 6
includes taxes & 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
Luxury Private Estate in the Berkshires | Whitney by AvantStay
Sheffield MA
8.6/10 Excellent! (14 reviews)
Great quiet house.
Reviewed on Oct 17, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Apr 30 to May 1
CA $120
CA $165 total
Apr 30 - May 1
includes taxes & fees
9/10 Wonderful! (890 reviews)
very clean and friendly staff
Reviewed on Mar 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.
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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.
