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.
Hilton Albany
Downtown Albany
Price was CA $1,069, price is now CA $1,009 per person
CA $1,009
per person
Jul 31 - Aug 2
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.2/10 Good! (1,004 reviews)
The Hilton hotel was cleaned I had a excellent experience I would recommend it
Reviewed on May 9, 2026
Hampton Inn Albany-Wolf Road (Airport)
Price was CA $1,124, price is now CA $1,042 per person
CA $1,042
per person
Jul 31 - Aug 2
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (1,004 reviews)
The breakfast menu was fresh. The staff replenished the food as it ran out. The food area was clean and organized.
Reviewed on May 16, 2026
Park Manor Hotel
Price was CA $1,202, price is now CA $1,128 per person
CA $1,128
per person
Jul 31 - Aug 2
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.8/10 Good! (1,285 reviews)
It’s ok for the price, but property condition is rough and it needs deep clean.
Reviewed on May 16, 2026
Hampton Inn & Suites Albany-Downtown
Downtown Albany
Price was CA $1,117, price is now CA $1,051 per person
CA $1,051
per person
Jul 31 - Aug 2
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (1,060 reviews)
We had to switch rooms due to a leaking shower. Somehow it was leaking into the room. Additionally the shower was “handicap” accessible but also sprayed water all over the bathroom floor. However they immediately moved us upon complaint.
Reviewed on Apr 20, 2026
Best Western Plus Franklin Square Inn Troy/Albany
Price was CA $1,199, price is now CA $1,129 per person
CA $1,129
per person
Jul 31 - Aug 2
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (1,004 reviews)
Very close to Troy Theater, nice location , beautiful view of water & right next to a BBQ place .
Reviewed on May 12, 2026
Sheffield Hotel Deals
Wilder House Berkshires
48 S Main Street Sheffield MA
Fully refundableReserve now, pay when you stay
The price is CA $226 per night from May 20 to May 21
CA $226
CA $252 total
May 20 - May 21
includes taxes & fees
9.8/10 Exceptional! (48 reviews)
Very comfortable bed, that was mostly what I cared about. I got my beauty sleep)
Reviewed on May 11, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from May 24 to May 25
CA $121
CA $165 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (937 reviews)
Really clean, great staff. Pool & hot tub A+
Reviewed on May 17, 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from May 20 to May 21
CA $172
CA $192 total
May 20 - May 21
includes taxes & fees
9/10 Wonderful! (949 reviews)
The images for the Inn didn’t show it was basically a motel. The rooms were loud because of traffic but more, because the heating unit made a terrible racket. You have to drag your luggage up several flights of stairs. The main host was a lovely woman! But the staffer who came to the room to adjust ...
Reviewed on May 17, 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.
